29841-69-8

Basic information

• Product Name: (1S,2S)-(-)-1,2-Diphenyl-1,2-ethanediamine
• Synonyms: 1,2-ETHANEDIAMINE, 1,2-DIPHENYL-, (1S,2S)-;(1S,2S)-(-)-1,2-DIPHENYL-1,2-ETHANEDIAMINE;(1S,2S)-(+)-1,2-DIPHENYL 1,2-ETHANEDIAMINE;(1S,2S)-1,2-DIPHENYL-1,2-ETHANEDIAMINE;(1S,2S)-(-)-1,2-DIAMINO-1,2-DIPHENYLETHANE;(1S,2S)-(+)-1,2-DIAMINO-1,2-DIPHENYLETHANE;(1S,2S)-(-)-1,2-DIPHENYL-1,2-ETHYLENEDIAMINE;(1S,2S)-1,2-DIPHENYL-ETHANE-1,2-DIAMINE
• CAS NO: 29841-69-8
• Molecular Formula: C₁₄H₁₆N₂
• Molecular Weight: 212.29
• EINECS: -0
• Product Categories: chiral;Chiral reagent;CHIRAL COMPOUNDS;Amines (Chiral);Analytical Chemistry;Asymmetric Synthesis;Chiral Building Blocks;e.e. / Absolute Configuration Determination (NMR);Enantiomer Excess & Absolute Configuration Determination;Synthetic Organic Chemistry;Amines and Derivatives;CHIRAL CHEMICALS;Chiral Compound;organic amine;Aromatics;Chiral Reagents;Miscellaneous Reagents;Chiral Nitrogen;DPEN Series
• Mol File: 29841-69-8.mol
• Article Data: 38

Chemical Properties

• Melting Point: 83-85 °C(lit.)
• Boiling Point: 342.14°C (rough estimate)
• Flash Point: 199.9 °C
• Appearance: white to pale yellow/crystal
• Density: 1.0799 (rough estimate)
• Vapor Pressure: 3.48E-05mmHg at 25°C
• Refractive Index: -103 ° (C=1, EtOH)
• Storage Temp.: 2-8°C
• PKA: 9.78±0.10(Predicted)
• Water Solubility: Insoluble in water.
• Sensitive: Air Sensitive
• BRN: 3201645
• CAS DataBase Reference: (1S,2S)-(-)-1,2-Diphenyl-1,2-ethanediamine(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-(-)-1,2-Diphenyl-1,2-ethanediamine(29841-69-8)
• EPA Substance Registry System: (1S,2S)-(-)-1,2-Diphenyl-1,2-ethanediamine(29841-69-8)

Safety Data

• Hazard Codes: Xi,C
• Statements: 36/37/38-34
• Safety Statements: 26-36-45-36/37/39
• RIDADR: UN3259
• WGK Germany: 3
• F: 10-23
• HazardClass: 8
• Hazardous Substances Data: 29841-69-8(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

(1S,2S)-(-)-1,2-Diphenyl-1,2-ethanediamine solvation agent, For synthesis of enantiopure ethylenediamines by chirality transfer (condensation with diketones followed by reductive cleavage), Co-catalyst in the Ru catalyzed enantioselective hydrogenation of aromatic ketones, Versatile ligand for the formation of metal complexes.1 Used in the synthesis of chiral tropocoronands which have potential utility in asymmetric catalysis

General Description

1,2-Diphenylethylenediamine is a chiral molecule, generally used as a chiral resolving agent and as a precursor of the chiral auxiliary. It is also used as a chiral solvating agent in NMR study.

InChI:InChI=1/C14H16N2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13-14H,15-16H2/t13-,14-/m0/s1

Synthetic route

rac-1,2-diphenylethylene-1,2-diamine (951-87-1, 5700-60-7, 16635-95-3, 29841-69-8, 35132-20-8, 107133-00-6) → (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8)

Conditions	Yield
Stage #1: rac-1,2-diphenylethylene-1,2-diamine With di-μ-Cl-bis{(SCRN)2-[1(N-i-PrNH)Et]Ph-C,N}diPd(II) In methanol for 1h; Substitution; Stage #2: With hydrogenchloride In dichloromethane for 0.0833333h; Decomposition;	85%
	60%
With L-(+)-tartaric acid Inert atmosphere;	38%

benzylidenamine (16118-22-2) → (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) + (R,R)-1,2-diphenylethylenediamine (35132-20-8)

Conditions	Yield
Stage #1: benzylidenamine With (5R,5'R)-4,4,4',4'-tetrakis(2,5-dimethylphenyl)-5,5'-diphenyl-2,2'-bi(1,3,2-dioxaborolane) In tetrahydrofuran; methanol at 20 - 30℃; Schlenk technique; Inert atmosphere; Sealed tube; Stage #2: With hydrogenchloride In methanol; water pH=Ca. 3; Catalytic behavior; Reagent/catalyst; Solvent;	A n/a B 80%
Stage #1: benzylidenamine With (5R,5'R)-5,5'-diphenyl-4,4,4',4'-tetra-o-tolyl-2,2'-bi(1,3,2-dioxaborolane) In tetrahydrofuran; methanol at 20℃; for 24h; Stage #2: With hydrogenchloride In methanol Reagent/catalyst; enantioselective reaction;	A n/a B n/a

C4H6O6*(x)C14H16N2 → (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8)

Conditions	Yield
With sodium hydroxide In dichloromethane; water at 0 - 5℃;	66%

1,2-Diphenyl-N,N'-bis-[1,7,7-trimethyl-bicyclo[2.2.1]hept-(2E)-ylidene]-ethane-1,2-diamine (137359-92-3, 137767-94-3) → (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8)

Conditions	Yield
With hydroxylamine acetate In ethanol for 24h; Heating;	50%

(+)-(1S,2S)-N-acetyl-N'-benzoyl-1,2-diamino-1,2-diphenylethane → (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8)

Conditions	Yield
With hydrogen bromide; acetic acid	49%

(+)-(1S,2S)-N-[(R)-α-acetoxyphenylacetyl]-N'-benzoyl-1,2-diamino-1,2-diphenylethane (911306-54-2) → (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8)

Conditions	Yield
With hydrogen bromide In acetic acid for 26h; Heating;	34%

(+)-(1S,2S)-1,2-diphenylethane-1,2-diazide (132486-62-5) → (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethyl acetate under 38000 Torr; Yield given;
With lithium aluminium tetrahydride In diethyl ether

threo-1,2-diphenyl-1,2-ethanediamin → (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8)

(S,S)-(-)-1,2-diphenylethane-1,2-diamine D-mandelate → (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8)

benzildioxime (23873-81-6) → (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) + meso-1,2-diphenyl-1,2-diaminoethane (951-87-1, 5700-60-7, 16635-95-3, 29841-69-8, 35132-20-8, 107133-00-6) + (R,R)-1,2-diphenylethylenediamine (35132-20-8)

Conditions	Yield
With sodium In ethanol for 0.166667h; Heating; Yield given. Yields of byproduct given;

1,2-Diphenylethylenediamine (5700-60-7) → (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8)

Conditions	Yield
via co-crystalization with N*-chiral dimeric ortho-palladated matrix SCRN-L>PdCl>2 L=2-<1-(N-isopropylamino)ethyl>phenyl-CN;

ditartrate of inactive α.α'-diphenyl-ethylenediamine → (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) + 1,2-diphenylethane-1,2-diamine (951-87-1, 5700-60-7, 16635-95-3, 29841-69-8, 35132-20-8, 107133-00-6)

Conditions	Yield
With water Durch fraktionierte Krystallisation;

(-)-(4S,5S)-4,5-dihydro-2,4,5-triphenyl-1H-imidazole (133815-20-0) → (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NaOAc 1.2: 95 percent / HCl / H2O 2.1: 49 percent / HBr; AcOH View Scheme

isoamarine (33722-46-2) → (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: NaOAc 1.2: 95 percent / HCl / H2O 2.1: 49 percent / HBr; AcOH View Scheme
Multi-step reaction with 3 steps 1: 68 percent / dicyclohexylcarbodiimide / CH2Cl2 / -20 - 20 °C 2: 92 percent / HCl / H2O; tetrahydrofuran / 2 h / Heating 3: 34 percent / aq. HBr / acetic acid / 26 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 1) Ac2O, 2) dil. HCl, 3) aq. HBr / 3) AcOH, reflux 2: 60 percent View Scheme

(-)-(4S,5S)-1-[(R)-α-acetoxyphenylacetyl]-4,5-dihydro-2,4,5-triphenyl-1H-imidazole (911306-52-0) → (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / HCl / H2O; tetrahydrofuran / 2 h / Heating 2: 34 percent / aq. HBr / acetic acid / 26 h / Heating View Scheme

(-)-(4RS,5RS)-1-[(R)-α-acetoxyphenylacetyl]-4,5-dihydro-2,4,5-triphenyl-1H-imidazole → (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: HCl / H2O; tetrahydrofuran / 2 h / Heating 2: 34 percent / aq. HBr / acetic acid / 26 h / Heating View Scheme

DL-(4R,5S)-2,4,5-triphenyl-4,5-dihydro-1H-imidazole (573-33-1, 973-15-9, 24427-33-6, 33722-46-2, 37134-88-6, 133815-20-0) → (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 70 percent / aq. NaOH / bis-(2-hydroxy-ethyl) ether / 0.75 h / 155 °C 2: 68 percent / dicyclohexylcarbodiimide / CH2Cl2 / -20 - 20 °C 3: 92 percent / HCl / H2O; tetrahydrofuran / 2 h / Heating 4: 34 percent / aq. HBr / acetic acid / 26 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 87 percent / aq. NaOH / bis-(2-hydroxy-ethyl) ether / 155 °C 2: 1) Ac2O, 2) dil. HCl, 3) aq. HBr / 3) AcOH, reflux 3: 60 percent View Scheme

(R,R)-(+)-4,5-diphenyl-1,3,2-dioxathiolan-2-one (183184-04-5) → (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 81 percent / LiN3 / dimethylformamide / 120 °C 2: pyridine 3: LiN3 / dimethylformamide / 120 °C 4: H2 / 10percent Pd/C / ethyl acetate / 38000 Torr View Scheme

(R,R)-hydroxybenzoin (52340-78-0) → (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: 100 percent / SOCl2 / CCl4 / Heating 2: 81 percent / LiN3 / dimethylformamide / 120 °C 3: pyridine 4: LiN3 / dimethylformamide / 120 °C 5: H2 / 10percent Pd/C / ethyl acetate / 38000 Torr View Scheme
Multi-step reaction with 3 steps 1: pyridine 2: NaN3 / dimethylformamide 3: LiAlH4 / diethyl ether View Scheme

(1R,2S)-2-azido-1,2-diphenylethan-1-ol (133522-22-2) → (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine 2: LiN3 / dimethylformamide / 120 °C 3: H2 / 10percent Pd/C / ethyl acetate / 38000 Torr View Scheme

Methanesulfonic acid (1R,2S)-2-azido-1,2-diphenyl-ethyl ester → (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: LiN3 / dimethylformamide / 120 °C 2: H2 / 10percent Pd/C / ethyl acetate / 38000 Torr View Scheme

(-)-(1R,2R)-1,2-diphenyl-1,2-ditosyloxyethane (132486-61-4) → (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaN3 / dimethylformamide 2: LiAlH4 / diethyl ether View Scheme

(E)-1,2-diphenyl-ethene (103-30-0) + sodium powder → (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) NaN3, Fe2(SO4)3, (ii) H2O2, (iii) Sn, aq. HCl View Scheme

C14H16N2*C33H24N2O7 → C33H24N2O7 + (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8)

Conditions	Yield
In ethanol; water Equilibrium constant; enantioselective reaction;

C14H16N2*C47H38O4 (1236286-39-7) → (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) + [(4R,5R)-2,2-dimethyl-1,3-dioxolan-4,5-diyl]bis(dinaphthalen-2-ylmethanol) (137365-09-4)

Conditions	Yield
In chloroform-d1 Equilibrium constant;

1,2-Diphenylethylenediamine (5700-60-7) → (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) + (R,R)-1,2-diphenylethylenediamine (35132-20-8)

Conditions	Yield
With chiral stationary phase including isopropyl-functionalized CF6 In methanol; acetic acid; triethylamine; acetonitrile at 0℃; Purification / work up;

N-benzoyl-N'-benzylidene-meso-1,2-diphenyl-ethylendiamine (1414364-68-3) → (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8)

Conditions	Yield
With sulfuric acid for 1h; Reflux;

4,5-diphenyl-4,5-dihydro-1H-imidazole → (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) + (R,R)-1,2-diphenylethylenediamine (35132-20-8)

Conditions	Yield
With barium(II) hydroxide In water at 80℃; for 23h; Overall yield = 93 %; enantioselective reaction;	A n/a B n/a

2,2-ppirocyclohexane-4,5-diphenyl-2H-imidazole (5396-98-5) → (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: ammonia; lithium / tetrahydrofuran; ethanol / -78 - -65 °C / Inert atmosphere 1.2: -65 °C / Inert atmosphere 1.3: 0 °C / Inert atmosphere 2.1: ethanol / 20 - 70 °C 3.1: sodium hydroxide / water; dichloromethane / 0 - 5 °C View Scheme

pyridine-2-carbaldehyde (1121-60-4) + (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) → (1S,2S)-N,N'-bis(2-pyridylmetheno)-1,2-diphenylethylenediimine

Conditions	Yield
In benzene for 2h; Heating;	100%
In methanol	22%

formaldehyd (50-00-0) + (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) → (4S,5S)-1,3-Dimethyl-4,5-diphenyl-imidazolidine

Conditions	Yield
With formic acid Heating;	100%

P,P-dichlorophenylphosphine oxide (824-72-6) + (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) → (S3,S4)-1-phenyl-(3,4-diphenyl)diazaphospholidine 1-oxide

Conditions	Yield
With triethylamine In dichloromethane	100%

carbon disulfide (75-15-0) + (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) → (4S,5S)-4,5-diphenylimidazolidine-2-thione (246868-60-0)

Conditions	Yield
In ethanol at 95℃; for 4h; Inert atmosphere;	100%
In ethanol at 95℃;

(S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) + (R)-2-phenyl-N-tosylaziridine (24395-14-0, 149769-84-6, 151003-26-8, 62596-62-7) → 4-methyl-N-[(1R)-2-{[(1S,2S)-2-{[(2R)-2-(4-methylbenzenesulfonamido)-2-phenylethyl]amino}-1,2-diphenylethy]amino}-1-phenylethyl]benzene-1-sulfonamido (1244040-50-3)

Conditions	Yield
In acetonitrile Reflux;	100%
In acetonitrile for 72h; Inert atmosphere; Reflux;	74%
In acetonitrile for 72h; Reflux;	74%

RuBr2[(S,S)-xylskewphos] + (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) → C51H62Br2N2P2Ru + C51H62Br2N2P2Ru

Conditions	Yield
In N,N-dimethyl-formamide at 25℃; for 17h; Inert atmosphere; Schlenk technique;	A 100% B n/a

2-bromoanisole (578-57-4) + (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) → (1R,2R)-N1,N2-bis(2-methoxyphenyl)-1,2-diphenylethane-1,2-diamine

Conditions	Yield
Stage #1: (S,S)-1,2-diphenyl-1,2-diaminoethane With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 20℃; for 1.5h; Inert atmosphere; Schlenk technique; Glovebox; Stage #2: 2-bromoanisole In toluene at 120℃; for 9h; Inert atmosphere; Schlenk technique; Glovebox;	100%

(S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) + 1,1′-((1R,2R)-1,2-diphenylethane-1,2-diyl)bis(3-(5-(tert-butyl)-3-formyl-2-hydroxybenzyl)-1H-imidazol-3-ium)dichloride → (1R,2R)-(-)-N,N′-bis(3-tert-butyl-5-diyl-1-ylmethyl-salicyliden)-[(1R,2R)-1,2-di(1H-imidazol-3-ium)-1,2-diphenylethane]-1,2-diphenylethan-diamin-dichloride

Conditions	Yield
In ethanol at 20℃; for 20h; Inert atmosphere; Molecular sieve;	100%

(S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) + (Ra)-1,1′-(6,6′-dimethyl-[1,1′-biphenyl]-2,2′-diyl)bis(3-(5-(tert-butyl)-3-formyl-2-hydroxybenzyl)-1H-imidazol-3-ium)dichloride → (1R,2R)-(-)-N,N′-bis(3-tert-butyl-5-diyl-1-ylmethyl-salicyliden)-[(Ra)-1,1′-(6,6′-dimethyl-[1,1′-biphenyl]-2,2′-diyl)bis(1H-imidazol-3-ium)]-1,2-diphenylethan-diamin-dichloride

Conditions	Yield
In ethanol at 20℃; for 20h; Inert atmosphere; Molecular sieve;	100%

(R)-camphorquinone (10334-26-6) + (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) → (1R,4S,5S)-4,5-diphenyl-1,11,11-trimethyl-3,6-diazatricyclo[6.2.1.02,7]undeca-2,6-diene (287379-86-6)

Conditions	Yield
In benzene Condensation; Heating;	99%

(S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) + Glyoxilic acid (298-12-4) → (4S,5S)-4,5-diphenylimidazolidine-2-carboxylic acid

Conditions	Yield
In dichloromethane for 16h;	99%
In dichloromethane for 16h;	99%

RuCl2{2,2'-bis(diphenylphosphinyl)benzophenone}(DMF)n + (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) → RuCl2{2,2'-bis(diphenylphosphinyl)benzophenone}{(S,S)-diphenylethylenediamine}

Conditions	Yield
In dichloromethane for 0.5h;	99%

RuCl2{2-diphenylphosphinobenzhydrol}(DMF)n + (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) → RuCl2{2-diphenylphosphinobenzhydrol}{(S,S)-diphenylethylenediamine}

Conditions	Yield
In dichloromethane for 0.5h;	99%

RuCl2{bis(2-diphenylphosphinophenyl)ether}(DMF)n + (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) → RuCl2{bis(2-diphenylphosphinophenyl)ether}{(S,S)-diphenylethylenediamine}

Conditions	Yield
In dichloromethane for 0.5h;	99%

[Rh{2,2'-bis(diphenylphosphinyl)benzophenone}(cod)(SbF6)] + (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) → RhCl2{2,2'-bis(diphenylphosphinyl)benzophenone}{(S,S)-diphenylethylenediamine}(SbF6)

Conditions	Yield
With hydrogen In dichloromethane for 1h;	99%

(S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) + 3,4-dimethoxybenzene-1-sulfonyl chloride (23095-31-0) → (S,S)-N-(2-amino-1,2-diphenyl-ethyl)-3,4-dimethoxy-benzenesulfonamide (953805-42-0)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	99%

(S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) + chloroformic acid ethyl ester (541-41-3) → diethyl ((1S,2S)-1,2-diphenylethane-1,2-diyl)dicarbamate (234753-20-9)

Conditions	Yield
With potassium carbonate In tetrahydrofuran; water at 0 - 20℃; for 4h;	98%
In ethanol Ambient temperature;
With pyridine In benzene for 2h;

(S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) + 2-formylbenzene boronic acid (40138-16-7) + (R)-1,1'-Bi-2-naphthol (18531-94-7) → (4S,5S)-2-(2-((Ra)-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaborepin-4-yl)phenyl)-4,5-diphenylimidazolidine

Conditions	Yield
In chloroform at 20℃; for 1h;	98%

(S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) + 2-bromo-4-methyl-1,1'-biphenyl (29180-98-1) → C27H26N2 (1192944-48-1)

Conditions	Yield
With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 110℃; for 48h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere;	98%
With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 100℃; for 10h; Inert atmosphere;	86.3%

di-μ-chlorobis[1-[2-(di-tert-butulphosphino)phenyl]ethyl-C1,P]dipalladium(II) (41077-10-5, 35886-08-9, 1266828-65-2) + (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) → (R,SS)/(S,SS)-[1-[2-(di-tert-butulphosphino)phenyl]ethyl-C1,P](1,2-diphenylethane-1,2-diamine-N,N)palladium(II) chloride

Conditions	Yield
In methanol (Ar, Schlenk) a suspn. of dimer and diamine in anhyd. CH3OH was stirred for 1 h at room temp.; filtered, evapd. to dryness;	98%

(S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) + ethyl acetimidate hydrochloride (2208-07-3) → (4S,5S)-2-methyl-4,5-diphenyl-4,5-dihydro-1H-imidazole (109830-48-0, 133815-21-1)

Conditions	Yield
In ethanol at 0 - 20℃; for 12h; Inert atmosphere;	98%

(S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) + Glyoxilic acid (298-12-4) → (4R,5R)-4,5-diphenyl-4,5-dihydro-1H-imidazole

Conditions	Yield
With N-Bromosuccinimide In methanol at 20℃; for 1h; Inert atmosphere;	98%
Stage #1: (S,S)-1,2-diphenyl-1,2-diaminoethane; Glyoxilic acid In methanol Stage #2: With N-Bromosuccinimide	98%
With N-Bromosuccinimide

Pentafluoropyridine (700-16-3) + (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) → (S,S)-N,N’-bis(2,3,5,6-tetrafluoropyridin-4-yl)-1,2-diphenylethane-1,2-diamine

Conditions	Yield
With triethylamine In tetrahydrofuran for 24h; Inert atmosphere; Reflux; regioselective reaction;	98%

(S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) + Ru(OAc)2(CO)((R)-Josiphos) → [Ru(OAc)(CO)((S,S)-dpen)(R-Josiphos)]OAc

Conditions	Yield
In (2)H8-toluene at 20℃; for 2h;	98%

trifluoromethylsulfonic anhydride (358-23-6) + (S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) → (1S,2S)-1,2-diphenyl-N,N'-bis(trifluoromethanesulfonyl)ethane-1,2-diamine (121788-77-0)

Conditions	Yield
With triethylamine In dichloromethane	97%
With dmap; triethylamine In dichloromethane at -78 - 20℃;	69%
With dmap; triethylamine In dichloromethane at -78 - 20℃; for 0.5h; Inert atmosphere;	57%

(S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) + phenyl isocyanate (103-71-9) → (+)-(1S,2S)-N,N'-dimethyl-1,2-diphenylethylenyl-diphenyl-diurea

Conditions	Yield
In dichloromethane Ambient temperature;	97%

(S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) + 5-bromo-3-tert-butyl-2-hydroxybenzaldehyde (153759-58-1) → (S,S)-2,2'-[(1,2-diphenyl-1,2-ethanediyl)bis(nitrilomethylidyne)]bis[4-bromo-6-(1,1-dimethylethy)phenol]

Conditions	Yield
In ethanol for 1h; Heating;	97%

(S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) + salicylaldehyde (90-02-8) → N,N'-Disalicyliden-meso-1,2-diphenylethylendiamin (41013-29-0, 41013-30-3, 51208-40-3, 58520-13-1, 61045-68-9, 61045-69-0, 132295-13-7)

Conditions	Yield
With sodium sulfate In methanol for 12h; Ambient temperature;	97%

(S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) + 2-Hydroxy-2'-methoxy-<1,1'-biphenyl>-3-carboxaldehyde (132939-08-3) → C42H36N2O4

Conditions	Yield
In ethanol at 20℃; for 24h;	97%

(S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) + 5-chloro-5H-dibenzo[a,d]cycloheptene (18506-04-2) → (S,S)-N,N'-bis(5H-dibenzo[a,d]cyclohepten-5-yl)-1,2-diphenyl-1,2-ethylenediamine (858370-95-3)

Conditions	Yield
With triethylamine In dichloromethane for 0.166667h; Heating;	97%
Stage #1: (S,S)-1,2-diphenyl-1,2-diaminoethane; 5-chloro-5H-dibenzo[a,d]cycloheptene In dichloromethane at 20℃; for 2.16667h; Stage #2: With potassium carbonate In dichloromethane; water	97%
In dichloromethane at 20℃; for 2.16667h;	97%

Upstream product

• 951-87-1 rac-1,2-diphenylethylene-1,2-diamine 
• 5396-98-5 2,3-diphenyl-1,4-diazaspiro[4.5]deca-1,3-diene 
• 134-81-6 benzil 
• 108-94-1 cyclohexanone 
• 6944-06-5 (+/-)-erythro-α'-acetylamino-α-benzamino-bibenzyl 
• 100-52-7 benzaldehyde 
• 573-33-1 amarine 
• 23873-81-6 benzildioxime 
• 155396-71-7 tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate 
• 522-34-9 Diphenylglyoxime 
• 572-45-2 benzil dioxime 
• 6944-06-5 threo-1-acetamido-2-benzamido-1,2-diphenylethane 
• 3190-04-3 (±)-2,3-diphenyl-1,4-diazaspiro[4.5]decane 
• 100-47-0 benzonitrile 

Downstream Products

• 31819-61-1 cis-5,6-diphenyl-piperazin-2-one 
• 35132-20-8 (R,R)-1,2-diphenylethylenediamine 
• 951-87-1 2-diphenyl-1,2-ethylenediamine 
• 60998-18-7 racem.-α.α'-bis-[1-(2-hydroxy-phenyl)-ethylidenamino]-bibenzyl 
• 642-04-6 2,3,5,6-tetraphenylpyrazine 
• 1244-95-7 N,N'-Bis-<2-methyl-butyliden-(3)>-meso-1,2-diamino-1,2-diphenyl-ethan 
• 1261-93-4 N_.N'-Bis-diisopentylmethylen-meso-1.2-diphenyl-aethylendiamin 
• 41013-29-0 N,N'-disalicylidene-(R,S)(S,R)-1,2-diphenyl-1,2-ethanediamine 
• 3190-15-6 N.N'-Bis-<1-propyl-aethyliden>-meso-1.2-diphenyl-aethylendiamin 
• 3190-05-4 N.N'-Bis-<2-dimethyl-propyliden>-meso-1.2-diphenyl-aethylendiamin 
• 64994-17-8 cis-5,6-diphenyl-[1,4,7]oxadiazonane 
• 41013-30-3 2,2'-[(1S,2S)-1,2-diphenyl-1,2-ethanediylbis(nitrilomethylidyne)]diphenol 
• 3190-20-3 N.N'-Bis-<β.β'-diphenyl-isopropyliden>-meso-1.2-diphenyl-aethylendiamin 
• 81401-20-9 meso-N,N'-bis(β-hydroxyethyl)-1,2-diphenyl-1,2-ethylenediamine 

Relevant articles and documents

Optical resolution of racemic stilbenediamine using N*-chiral ortho-palladated matrix

Optical resolution of racemic stilbenediamine (Stien) was performed by recrystallization of its diastereomeric adducts with ortho-palladated (S)-N-isopropyl-α-methylbenzylamine. The less soluble (SCRN,SS) diasteteomer was studied by X-ray diffraction analysis. It was established that the crystal of this diastereomer consists of dimers formed via association of two molecules of the mononuclear cationic complex with an additional molecule of free diamine of the same absolute configuration. The association occurs through a system of hydrogen bonds and weak agostic interactions. Based on the X-ray diffraction data, the procedure was improved for the resolution of stilbenediamine due to the more profitable use of the ortho-palladated reagent. The Stien/Pd ratio in the diastereomer isolated was increased up to 3 : 2. The conformational features of the complex are discussed on the basis of 1H NMR spectroscopy data.

Improved Optical Resolution of (+/-)-1,2-Diphenylethylenediamine

(+/-)-1,2-Diphenylethylenediamine (DPEDA) was efficiently resolved by the fractional crystallization of its diastereomeric salts with optically active mandelic acid. 1H-NMR spectrum of N-monoacylated DPEDA with an optically active derivatizing agent showed that DPEDA thus obtained was optically pure.

Mechanistic studies inform design of improved Ti(salen) catalysts for enantioselective [3 + 2] cycloaddition

Ti(salen) complexes catalyze the asymmetric [3 + 2] cycloaddition of cyclopropyl ketones with alkenes. While high enantioselectivities are achieved with electron-rich alkenes, electron-deficient alkenes are less selective. Herein, we describe mechanistic studies to understand the origins of catalyst and substrate trends in an effort to identify a more general catalyst. Density functional theory (DFT) calculations of the selectivity determining transition state revealed the origin of stereochemical control to be catalyst distortion, which is largely influenced by the chiral backbone and adamantyl groups on the salicylaldehyde moieties. While substitution of the adamantyl groups was detrimental to the enantioselectivity, mechanistic information guided the development of a set of eight new Ti(salen) catalysts with modified diamine backbones. These catalysts were evaluated with four electron-deficient alkenes to develop a three-parameter statistical model relating enantioselectivity to physical organic parameters. This statistical model is capable of quantitative prediction of enantioselectivity with structurally diverse alkenes. These mechanistic insights assisted the discovery of a new Ti(salen) catalyst, which substantially expanded the reaction scope and significantly improved the enantioselectivity of synthetically interesting building blocks.

Enantioselective Reductive Coupling of Imines Templated by Chiral Diboron

We herein report a general, practical, and highly efficient method for asymmetric synthesis of a wide range of chiral vicinal diamines via reductive coupling of imines templated by chiral diboron. The protocol features high enantioselectivity and stereospecificity, mild reaction conditions, simple operating procedures, use of readily available starting materials, and a broad substrate scope. The method signifies the generality of diboron-enabled [3,3]-sigmatropic rearrangement.

Synergistic copper-TEMPO catalysis of intermolecular vicinal diamination of styrenes

A copper-catalyzed, 2,2,6,6-tetramethyl piperidine N-oxy radical-assisted intermolecular diamination of styrenes with N-fluorobenzenesulfonimide has been developed. The current protocol proved amenable to a diverse array of styrenes via cascade radical addition to readily afford synthetically useful aromatic vicinal diamines with exclusive diastereoselectivity.