22348-32-9

Basic information

• Product Name: (R)-(+)-alpha,alpha-Diphenyl-2-pyrrolidinemethanol
• Synonyms: diphenyl-[(2R)-pyrrolidin-2-yl]methanol;2-Pyrrolidinemethanol, α,α-diphenyl-, (2R)-;(2R)-α,α-diphenyl-2-Pyrrolidinemethanol;2-PYRROLIDINEMETHANOL, A,A-DIPHENYL-;ALPHA,ALPHA-DIPHENYL-D-PROLINOL;A,A-DIPHENYL-D-PROLINOL;(R)-1-DIPHENYL-PROLINOL;(R)-(+)-2-(DIPHENYLHYDROXYMETHYL)-PYRROLIDIN
• CAS NO: 22348-32-9
• Molecular Formula: C₁₇H₁₉NO
• Molecular Weight: 253.34
• EINECS: 1312995-182-4
• Product Categories: pharmacetical;chiral;CHIRAL COMPOUNDS;Chiral Reagent;Chiral Reagents;Benzenes;Asymmetric Synthesis;Chiral Building Blocks;Simple Alcohols (Chiral);Synthetic Organic Chemistry;CHIRAL CHEMICALS;Chiral chemicals;Peptide;Pharmaceutical intermediate
• Mol File: 22348-32-9.mol
• Article Data: 54

Chemical Properties

• Melting Point: 77-80 °C
• Boiling Point: 396.54°C (rough estimate)
• Flash Point: 133.3 °C
• Appearance: white to faintly yellow crystalline powder
• Density: 1.0078 (rough estimate)
• Vapor Pressure: 1.67E-07mmHg at 25°C
• Refractive Index: 58 ° (C=2, MeOH)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: almost transparency in Chloroform
• PKA: 13.15±0.29(Predicted)
• BRN: 4353363
• CAS DataBase Reference: (R)-(+)-alpha,alpha-Diphenyl-2-pyrrolidinemethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-alpha,alpha-Diphenyl-2-pyrrolidinemethanol(22348-32-9)
• EPA Substance Registry System: (R)-(+)-alpha,alpha-Diphenyl-2-pyrrolidinemethanol(22348-32-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• F: 10-34
• TSCA: No
• Hazardous Substances Data: 22348-32-9(Hazardous Substances Data)

Usage

Chemical Properties

white to faintly yellow crystalline powder

Uses

suzuki reaction

InChI:InChI=1/C17H19NO/c19-17(16-12-7-13-18-16,14-8-3-1-4-9-14)15-10-5-2-6-11-15/h1-6,8-11,16,18-19H,7,12-13H2/t16-/m1/s1

Synthetic route

2-(hydroxy(diphenyl)methyl)pyrrolidine-1-carboxylic acid tert-butyl ester (137496-68-5) → (R)-α,α-diphenylprolinol (22348-32-9)

Conditions	Yield
With sodium hydroxide In ethanol for 2.5h; Reflux;	100%
With sodium hydroxide In ethanol at 79℃; for 4h;	90%

(R)-1-tert-butyl-(λ1-oxidanyl)-(λ3-sulfanyl)-2-((methoxymethoxy)diphenylmethyl)pyrrolidine → (R)-α,α-diphenylprolinol (22348-32-9)

Conditions	Yield
Stage #1: (R)-1-tert-butyl-(λ1-oxidanyl)-(λ3-sulfanyl)-2-((methoxymethoxy)diphenylmethyl)pyrrolidine With hydrogenchloride In methanol at 0 - 70℃; for 4h; Stage #2: With sodium hydrogencarbonate In tetrahydrofuran; methanol at 20℃; for 6h;	91%

diphenyl(pyrrolidin-2-yl)methanol (63401-04-7) → (R)-α,α-diphenylprolinol (22348-32-9)

(R)-Tetrahydro-1H,3H-pyrrolo<1,2-c>oxazole-1,3-dione (90971-03-2) + phenylmagnesium chloride → (R)-α,α-diphenylprolinol (22348-32-9)

Conditions	Yield
In tetrahydrofuran Yield given;

diphenyl(pyrrolidin-2-yl)methanol (63401-04-7) → (S)-diphenylprolinol (22348-32-9, 63401-04-7, 112022-88-5, 112068-01-6) + (R)-α,α-diphenylprolinol (22348-32-9)

Conditions	Yield
Stage #1: diphenyl(pyrrolidin-2-yl)methanol With (R)-1,1'-Bi-2-naphthol; boric acid In acetonitrile Heating; Stage #2: With hydrogenchloride In diethyl ether; water Further stages.;

benzophenone (119-61-9) + zinc dust → (R)-α,α-diphenylprolinol (22348-32-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) s-BuLi, (-)-sparteine, 3.) AcOH 2: 90 percent / NaOH / ethanol / 4 h / 79 °C View Scheme

phenylmagnesium chloride → (R)-α,α-diphenylprolinol (22348-32-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 70 percent / tetrahydrofuran / 24 h / 23 °C 2: 77 percent / BH3 / tetrahydrofuran View Scheme

methyl 5-oxopyrrolidine-2-carboxylate (4931-66-2, 54571-66-3, 64700-65-8) → (R)-α,α-diphenylprolinol (22348-32-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 70 percent / tetrahydrofuran / 24 h / 23 °C 2: 77 percent / BH3 / tetrahydrofuran View Scheme

Pyroglutamic acid (149-87-1) → (R)-α,α-diphenylprolinol (22348-32-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 95 percent / 5 molpercent hydrogen chloride (from acetyl chloride) / 24 h / 23 °C 2: 70 percent / tetrahydrofuran / 24 h / 23 °C 3: 77 percent / BH3 / tetrahydrofuran View Scheme

5-(hydroxy-diphenyl-methyl)-pyrrolidin-2-one (21901-76-8) → (R)-α,α-diphenylprolinol (22348-32-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / BH3 / tetrahydrofuran View Scheme

C24H25NO (356790-44-8) → (R)-α,α-diphenylprolinol (22348-32-9)

Conditions	Yield
With hydrogenchloride; palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 18h; Inert atmosphere;

C20H23NO3 → (R)-α,α-diphenylprolinol (22348-32-9)

Conditions	Yield
With potassium hydroxide In methanol for 48h; Reflux;

phenylmagnesium chloride (100-59-4) + 1-(tert-butyl) 2-methyl (R)-pyrrolidine-1,2-dicarboxylate (73323-65-6) → (R)-α,α-diphenylprolinol (22348-32-9)

Conditions	Yield
Stage #1: phenylmagnesium chloride; 1-(tert-butyl) 2-methyl (R)-pyrrolidine-1,2-dicarboxylate In tetrahydrofuran at 10 - 60℃; Industrial scale; Stage #2: With hydrogenchloride In water at 45℃; for 9h; Industrial scale; Stage #3: With sodium hydroxide Industrial scale;	n/a

((methoxymethoxy)methylene)dibenzene (223930-75-4) → (R)-α,α-diphenylprolinol (22348-32-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N,N,N,N,-tetramethylethylenediamine; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -40 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: hydrogenchloride / methanol / 4 h / 0 - 70 °C 2.2: 6 h / 20 °C View Scheme

3-chloro-n-propanesulfonyl chloride (1633-82-5) + (R)-α,α-diphenylprolinol (22348-32-9) → (R)-(1-(3-chloropropylsulfonyl)pyrrolidin-2-yl)diphenylmethanol (1370293-21-2)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;	100%

Triisopropyl borate (5419-55-6) + (R)-α,α-diphenylprolinol (22348-32-9) + ethylene glycol (107-21-1) → (R)-2-[(1,3,2-dioxaborolan-2-yloxy)diphenylmethyl]pyrrolidine

Conditions	Yield
In toluene at 80℃; for 1h; Inert atmosphere;	100%
Stage #1: Triisopropyl borate; ethylene glycol In toluene Inert atmosphere; Reflux; Stage #2: (R)-α,α-diphenylprolinol In toluene at 80℃; for 1h; Inert atmosphere; Reflux;	100%
Stage #1: Triisopropyl borate; ethylene glycol In toluene Inert atmosphere; Reflux; Stage #2: (R)-α,α-diphenylprolinol In toluene at 80℃; for 1h; Inert atmosphere;	90%

phenylbis(diisopropylamino)borane (47127-05-9) + (R)-α,α-diphenylprolinol (22348-32-9) → (S)-tetrahydro-1,3,3-triphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazoborolidine

Conditions	Yield
In tetrahydrofuran; toluene reflux for 30 min; solvents are removed;	96%

butylbis(diisopropylamino)borane (151293-62-8) + (R)-α,α-diphenylprolinol (22348-32-9) → (S)-tetrahydro-1-butyl-3,3-diphenyl-1H,3H-pyrrolo{2,1-c}{1,3,2}oxazaborole

Conditions	Yield
In tetrahydrofuran; toluene reflux for 30 min; solvents are removed;	95%

chloromethyldiphenylsilane (144-79-6) + (R)-α,α-diphenylprolinol (22348-32-9) → (R)-2-(((methyldiphenylsilyl)oxy)diphenylmethyl)pyrrolidine

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 24h;	93%

(R)-α,α-diphenylprolinol (22348-32-9) + 2-iodo-4,4-dimethyl-cyclohex-2-enone (157952-85-7) → (S)-2-iodo-4,4-dimethyl-2-cyclohexen-1-ol

Conditions	Yield
Stage #1: (R)-α,α-diphenylprolinol With Trimethyl borate In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: 2-iodo-4,4-dimethyl-cyclohex-2-enone With N,N-diethylaniline borane In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;	92%

(R)-α,α-diphenylprolinol (22348-32-9) + N-((2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)-methyl)-tetrahydro-2H-pyran-2-yl)-2,2,2-trichloroacetamide (99701-64-1) → C52H54N2O7 (1158857-93-2)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 25℃; Inert atmosphere;	90%
With caesium carbonate In N,N-dimethyl-formamide at 25℃; Schlenk technique; Inert atmosphere;	90%

(R)-α,α-diphenylprolinol (22348-32-9) + ethylene glycol (107-21-1) → (R)-2-[(1,3,2-dioxaborolan-2-yloxy)diphenylmethyl]pyrrolidine

Conditions	Yield
With Triisopropyl borate	90%
Stage #1: ethylene glycol With Triisopropyl borate In toluene at 105℃; Inert atmosphere; Stage #2: (R)-α,α-diphenylprolinol In toluene for 1h; Inert atmosphere;

methylbis(diisopropylamino)borane (151293-60-6) + (R)-α,α-diphenylprolinol (22348-32-9) → (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole (112022-81-8)

Conditions	Yield
In tetrahydrofuran; toluene reflux for 30 min; solvents are removed;	89%

(R)-α,α-diphenylprolinol (22348-32-9) + 2-Nitrobenzenesulfonyl chloride (1694-92-4) → (R)-(1-((2-nitrophenyl)sulfonyl)pyrrolidin-2-yl)diphenylmethanol

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	85%

dihydroxy-methyl-borane (13061-96-6) + (R)-α,α-diphenylprolinol (22348-32-9) → (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole (112022-81-8)

Conditions	Yield
In n-heptane at 40℃; Solvent; Temperature; Inert atmosphere; Reflux; Large scale;	83%

2,6-bis-(bromomethyl)pyridine (7703-74-4) + (R)-α,α-diphenylprolinol (22348-32-9) → (2R,2'R)-1,1'-(pyridine-2,6-diylbis(methylene))bis[2-(diphenylmethanol)pyrrolidine] (1310579-92-0)

Conditions	Yield
With potassium carbonate; potassium iodide In ethanol at 20℃; for 8h;	78%

2-(bromomethyl)pyridine hydrobromide (31106-82-8) + (R)-α,α-diphenylprolinol (22348-32-9) → (R)-2-(diphenylmethanol)-1-(pyridin-2-ylmethyl)pyrrolidine (132902-42-2)

Conditions	Yield
With potassium carbonate; potassium iodide In ethanol at 20℃; for 10h;	76%

(R)-α,α-diphenylprolinol (22348-32-9) + 4-(2,4-dioxo-1,2,3,4-tetrahydro-1-pyrimidinyl)butanoic acid (2950-83-6) → (R)-1-(4-(2-(hydroxydiphenylmethyl)pyrrolidin-1-yl)-4-oxobutyl)pyrimidine-2,4(1H,3H)-dione (1204659-22-2)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 3h;	66%

(R)-α,α-diphenylprolinol (22348-32-9) + N-Benzyloxycarbonyl-L-proline (1148-11-4) → (S)-2-[(R)-2-(Hydroxy-diphenyl-methyl)-pyrrolidine-1-carbonyl]-pyrrolidine-1-carboxylic acid benzyl ester

Conditions	Yield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In chloroform for 12h;	65%

(R)-α,α-diphenylprolinol (22348-32-9) + 4-chlorophenylglyoxal (4998-15-6) → 1-(4-chlorophenyl)-2-[2-(diphenylmethylene)pyrrolidin-1-yl]ethane-1,2-dione (1620212-19-2)

Conditions	Yield
With gold(III) tribromide In dichloromethane at 60℃; for 12h; Schlenk technique;	62%

t-butyldimethylsiyl triflate (69739-34-0) + (R)-α,α-diphenylprolinol (22348-32-9) → (R)-2-(((tert-butyldimethylsilyl)oxy)diphenylmethyl)pyrrolidine (1236033-34-3)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 22℃; for 12h; Inert atmosphere;	56%

(2-formylphenyl)(diphenyl)phosphine (50777-76-9) + (R)-α,α-diphenylprolinol (22348-32-9) → (2R,5R)-1-aza-2-(2-diphenylphosphino)phenyl-3-oxa-4,4-diphenylbicyclo[3.3.0]octane

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 24h; Cycloaddition; Heating;	54%

(1R,4R,7R)-7-isopropyl-5-methylbicyclo[2.2.2]octane-2,5-diene-2-carboxylic acid (1252606-18-0) + (R)-α,α-diphenylprolinol (22348-32-9) → ((R)-2-(hydroxydiphenylmethyl)pyrrolidin-1-yl)((1R,4R,7R)-7-isopropyl-5-methylbicyclo[2.2.2]octa-2,5-dien-2-yl)methanone

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In acetonitrile at 20℃; for 16h; Inert atmosphere; Schlenk technique;	31%

Trimethylboroxine (823-96-1) + (R)-α,α-diphenylprolinol (22348-32-9) → (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole (112022-83-0)

Conditions	Yield
In toluene Heating;
With borane In toluene at 20 - 150℃; for 4.5h;
In toluene at 20℃; for 0.5h;

Trimethyl borate (121-43-7) + (R)-α,α-diphenylprolinol (22348-32-9) → (R)-2-methoxy-CBS-oxazaborolidine

Conditions	Yield
With dimethylsulfide borane complex In tetrahydrofuran at 45℃; for 10h;
In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
In tetrahydrofuran
In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
Stage #1: Trimethyl borate; (R)-α,α-diphenylprolinol In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Stage #2: With dimethylsulfide borane complex In tetrahydrofuran Inert atmosphere;

(R)-α,α-diphenylprolinol (22348-32-9) → (R)-(+)-2-methyl-CBS-oxazaborolidine

Conditions	Yield
With dimethylsulfide borane complex In tetrahydrofuran at 45℃; for 10h;
With dimethylsulfide borane complex In tetrahydrofuran; toluene at 20℃; for 1h; Inert atmosphere;
With borane-THF

tri-o-tolylboroxine (7294-50-0) + (R)-α,α-diphenylprolinol (22348-32-9) + bis(trifluoromethanesulfonyl)amide (82113-65-3) → (R)-(+)-3,3-diphenyl-1-o-tolyl-tetrahydropyrrolo-(1,2-c)(1,3,2)oxazaborole-1,1,1-trifluoro-N-((trifluoromethyl)-sulfonyl)methanesulfonamide

Conditions	Yield
Stage #1: tri-o-tolylboroxine; (R)-α,α-diphenylprolinol With 4A MS In toluene for 3h; Heating; Stage #2: bis(trifluoromethanesulfonyl)amide In dichloromethane at -25℃; for 0.25h;

tri-o-tolylboroxine + (R)-α,α-diphenylprolinol (22348-32-9) + bis(trifluoromethanesulfonyl)amide (82113-65-3) → (R)-(+)-3,3-diphenyl-1-o-tolyl-tetrahydropyrrolo-(1,2-c)(1,3,2)oxazaborole-1,1,1-trifluoro-N-((trifluoromethyl)-sulfonyl)methanesulfonamide

Conditions	Yield
Stage #1: tri-o-tolylboroxine; (R)-α,α-diphenylprolinol In toluene at 145℃; for 3h; Stage #2: bis(trifluoromethanesulfonyl)amide In toluene at -20℃; for 0.333333h;

tri-o-tolylboroxine (7294-50-0) + (R)-α,α-diphenylprolinol (22348-32-9) → (R)-2-(o-methyl)phenyl-CBS-oxazaborolidine

Conditions	Yield
In toluene Heating;
With 4 A molecular sieve In toluene Heating;
In toluene for 20h; Reflux;

Upstream product

• 63401-04-7 diphenyl(pyrrolidin-2-yl)methanol 
• 118970-95-9 (S)-1-benzyl-2-(hydroxydiphenylmethyl)pyrrolidine 
• 45736-33-2 (S)-proline-N-carboxyanhydride 
• 18620-02-5 (4-bromophenyl)magnesium bromide 
• 2133-40-6 L-proline methyl ester monohydrochloride 
• 77581-28-3 (S)-proline-N-ethyl carbamate methyl ester 
• 100-58-3 phenylmagnesium bromide 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 108-86-1 bromobenzene 
• 112022-81-8 (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole 
• 100-59-4 phenylmagnesium chloride 
• 59936-29-7 (S)-N-(tert-butoxycarbonyl)proline methyl ester 
• 90971-03-2 (R)-Tetrahydro-1H,3H-pyrrolo<1,2-c>oxazole-1,3-dione 
• 356790-44-8 C₂₄H₂₅NO 

Downstream Products

• 132902-42-2 (S)-2-(hydroxydiphenylmethyl)-1-(2'-pyridylmethyl)pyrrolidine 
• 171362-43-9 (R)-(+)-1-<(4-bromobenzenesulfinyl)>-<(2S)-(diphenylhydroxymethyl)>pyrrolidine 
• 204907-35-7 (1S,3αS)-1,3,3-triphenyltetrahydro-3Hpyrrolo[1,2-c][1,3,2]oxazaphosphole 1-oxide 
• 195195-95-0 (S)-2-(hydroxydiphenylmethyl)-1-(3'-pyridylmethyl)pyrrolidine 
• 163814-41-3 (S)-2-methoxydiphenylmethyl-1-(2-nitrovinyl)pyrrolidine 
• 360574-96-5 (S)-N-(pivaloyl)-α,α-diphenylpyrrolidine-2-methanol 
• 223714-08-7 (S)-2-diphenylhydroxymethyl-1-(2-nitrovinyl)pyrrolidine 
• 502159-06-0 1-chloro-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxaphosphole 
• 313216-34-1 (2S,5S)-2-phenoxy-4,4-diphenyl-1-aza-3-oxa-2-phosphabicyclo[3.3.0]octan-2-one 
• 129145-37-5 (S)-tetrahydro-1-butyl-3,3-diphenyl-1H,3H-pyrrolo{2,1-c}{1,3,2}oxazaborole 
• 335646-03-2 3-butoxy-4-[(2'S)-2'-(diphenylhydroxymethyl)pyrrolidino]-3-cyclobutene-1,2-dione 

Relevant articles and documents

London Dispersion Interactions Rather than Steric Hindrance Determine the Enantioselectivity of the Corey–Bakshi–Shibata Reduction

The well-known Corey–Bakshi–Shibata (CBS) reduction is a powerful method for the asymmetric synthesis of alcohols from prochiral ketones, often featuring high yields and excellent selectivities. While steric repulsion has been regarded as the key director of the observed high enantioselectivity for many years, we show that London dispersion (LD) interactions are at least as important for enantiodiscrimination. We exemplify this through a combination of detailed computational and experimental studies for a series of modified CBS catalysts equipped with dispersion energy donors (DEDs) in the catalysts and the substrates. Our results demonstrate that attractive LD interactions between the catalyst and the substrate, rather than steric repulsion, determine the selectivity. As a key outcome of our study, we were able to improve the catalyst design for some challenging CBS reductions.

Basicities and Nucleophilicities of Pyrrolidines and Imidazolidinones Used as Organocatalysts

The Br?nsted basicities pKaH (i.e., pKa of the conjugate acids) of 32 pyrrolidines and imidazolidinones, commonly used in organocatalytic reactions, have been determined photometrically in acetonitrile solution using CH acids as indicators. Most investigated pyrrolidines have basicities in the range 16 aH aH aH 12.6) and the 2-imidazoliummethyl-substituted pyrrolidine A21 (pKaH 11.1) are outside the typical range for pyrrolidines with basicities comparable to those of imidazolidinones. Kinetics of the reactions of these 32 organocatalysts with benzhydrylium ions (Ar2CH+) and structurally related quinone methides, common reference electrophiles for quantifying nucleophilic reactivities, have been measured photometrically. Most reactions followed second-order kinetics, first order in amine and first order in electrophile. More complex kinetics were observed for the reactions of imidazolidinones and several pyrrolidines carrying bulky 2-substituents, due to reversibility of the initial attack of the amines at the electrophiles followed by rate-determining deprotonation of the intermediate ammonium ions. In the presence of 2,4,6-collidine or 2,6-di-tert-butyl-4-methyl-pyridine, the deprotonation of the initial adducts became faster, which allowed the rate of the attack of the amines at the electrophiles to be determined. The resulting second-order rate constants k2 followed the correlation log?k2(20 °C) = sN(N + E), where electrophiles are characterized by one parameter (E) and nucleophiles are characterized by the two solvent-dependent parameters N and sN. In this way, the organocatalysts A1-A32 were integrated in our comprehensive nucleophilicity scale, which compares n-, -, and σ-nucleophiles. The nucleophilic reactivities of the title compounds correlate only poorly with their Br?nsted basicities.

Synthesis process of chiral catalyst

The invention relates to a low-cost efficient synthesis process of both a chiral catalyst chiral (R)-(+)-2-(Diphenylhydroxymethyl)pyrrolidine and a hydrochloride thereof. According to the process, rawmaterials which can be commercially obtained easily and are environmentally friendly are used; a one-kettle method is used for operation; through esterification reaction, Boc protecting group addition on amino group, Grignard reaction and Boc protecting group removal, high-optical-purity (R)-(+)-2-(Diphenylhydroxymethyl)pyrrolidine hydrochloride is obtained. The process is simplified; the production cost is reduced; the requirements of green chemistry at present are met. The content of (R)-(+)-2-(Diphenylhydroxymethyl)pyrrolidine and the hydrochloride thereof, prepared by the process, is higher than 99.0 percent; the optical purity is not smaller than 99.5 percent; the total yield is higher than 80 percent.