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Cas Database

53777-08-5

53777-08-5

Identification

  • Product Name:(2S)-2-Phenylbutane-2-ol

  • CAS Number: 53777-08-5

  • EINECS:

  • Molecular Weight:150.221

  • Molecular Formula: C10H14O

  • HS Code:

  • Mol File:53777-08-5.mol

Synonyms:(2S)-2-Phenylbutane-2-ol;(S)-1-Phenyl-1-methyl-1-propanol;(S)-2-Phenyl-2-butanol;(S)-2-Phenylbutane-2-ol;(S)-α-Methyl-α-ethylbenzenemethanol;[S,(-)]-α-Ethyl-α-methylbenzyl alcohol

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Relevant articles and documentsAll total 40 Articles be found

Asymmetric synthesis of tertiary vinyl carbinols by highly stereoselective methylation of α-methyl-β-ketosulfoxides with aluminum reagents

García Ruano, José L.,Rodríguez-Fernández, M. Mercedes,Maestro, M.Carmen

, p. 5701 - 5710 (2004)

Methylation of chiral acyclic α-methyl-β-ketosulfoxides with Me3Al and Me2AlCl is reported. Induced configuration at hydroxylic carbon is mainly controlled by the configuration of the sulfinyl group, with de's higher than 90% in most of the cases regardless the configuration at C-α. The stereochemical pathway seems to be different with both reagents, thus affording a higher stereoselectivity with Me 2AlCl. Pyrolytic desulfinylation and hydrogenolysis of the C-S bond allowed the transformation of the resulting hydroxysulfoxides into interesting optically pure tertiary methyl carbinols.

Harnessing the Power of the Asymmetric Grignard Synthesis of Tertiary Alcohols: Ligand Development and Improved Scope Exemplified by One-Step Gossonorol Synthesis

Gilheany, Declan G.,Kavanagh, Saranna E.

supporting information, p. 8198 - 8203 (2020/11/18)

A series of N-substituted cyclohexyldiaminophenolic ligands for the asymmetric Grignard synthesis of tertiary alcohols is reported. The 2,5-dimethylpyrrole-decorated ligand led to improved enantioselectivities and broadened the scope of the methodology. As an exemplar, we report an unprecedented highly selective one-step synthesis of gossonorol in 93% ee, also constituting the shortest formal syntheses of natural products boivinianin B and yingzhaosu C.

Very short highly enantioselective Grignard synthesis of 2,2-disubstituted tetrahydrofurans and tetrahydropyrans

Monasterolo, Claudio,Müller-Bunz, Helge,Gilheany, Declan G.

, p. 6531 - 6538 (2019/07/10)

Phenones with elongated chains are shown to be excellent substrates for ligand-promoted asymmetric Grignard synthesis of tertiary alcohols. In turn this enables the simple, short and highly enantioselective (up to 96% ee) preparation of chiral 2,2-disubst

Asymmetric Grignard Synthesis of Tertiary Alcohols through Rational Ligand Design

Bieszczad, Bartosz,Gilheany, Declan G.

supporting information, p. 4272 - 4276 (2017/04/03)

A simple, general and practical method is reported for highly enantioselective construction of tertiary alcohols through the direct addition of organomagnesium reagents to ketones. Discovered by rational ligand design based on a mechanistic hypothesis, it has an unprecedented broad scope. It utilizes a new type of chiral tridentate diamine/phenol ligand that is easily removed from the reaction mixture. It is exemplified by application to a formal asymmetric synthesis (>95:5 d.r.) of vitamin E.

CHIRAL DIAMINE COMPOUNDS FOR THE PREPARATION OF CHIRAL ALCOHOL AND CHIRAL AMINE

-

Page/Page column 64, (2015/12/17)

A process for the stereoselective preparation of a chiral alcohol or a chiral amine, the process comprising reacting a first prochiral reactant selected from the group consisting of a ketone, an aldehyde, and an inline, with a second reactant comprising a Grignard reagent, in the presence of a chiral trans-diamim of formula (1) as defined herein. Also provided is the use of the chiral trans-diamine of formula (1) in a Grignard reaction and the chiral trans-diamines per se.

QSAR analysis of the catalytic asymmetric ethylation of ketone using physical steric parameters of chiral ligand substituents

Huang, Huayin,Zong, Hua,Shen, Bin,Yue, Huifeng,Bian, Guangling,Song, Ling

supporting information, p. 1289 - 1297 (2014/02/14)

We have demonstrated that a validated QSAR (quantitative structure-activity relationship) model can be constructed between sterimol steric parameters of the N-substituents of chiral 1,2-amino-phosphoramide ligands and the enantiomeric ratios of alcohol products produced in the asymmetric additions of diethylzinc to acetophenone, which is powerful for predicting the steric effects of ligand substituents on enantioselectivities and instructive for ligand optimization.

Process route upstream and downstream products

Process route

diethylzinc
557-20-0

diethylzinc

acetophenone
98-86-2

acetophenone

dypnone
495-45-4

dypnone

(S)-2-phenyl-butan-2-ol
53777-08-5

(S)-2-phenyl-butan-2-ol

(R)-2-phenyl-butan-2-ol
1006-06-0

(R)-2-phenyl-butan-2-ol

Conditions
Conditions Yield
diethylzinc; With C56H43N2OP; In toluene; at -35 ℃; for 0.5h; Inert atmosphere;
acetophenone; In toluene; at -65 ℃; for 96h; enantioselective reaction; Inert atmosphere;
87 % ee
45 %Spectr.
diethylzinc
557-20-0

diethylzinc

acetophenone
98-86-2

acetophenone

2,3-diphenyl-2,3-butanediol
1636-34-6

2,3-diphenyl-2,3-butanediol

(S)-2-phenyl-butan-2-ol
53777-08-5

(S)-2-phenyl-butan-2-ol

(R)-2-phenyl-butan-2-ol
1006-06-0

(R)-2-phenyl-butan-2-ol

Conditions
Conditions Yield
With titanium(IV) isopropylate; calcium hydride; (1S,2R,4S)-N-(naphth-1-ylmethyl)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>hept-1-ylmethanesulfonamide; In toluene; at 4 ℃; for 96h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
16%
With titanium(IV) isopropylate; calcium hydride; (2S)-N-(naphth-1-ylmethyl)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>hept-1-ylmethanesulfonamide; In toluene; at 4 ℃; for 96h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
13%
diethylzinc
557-20-0

diethylzinc

acetophenone
98-86-2

acetophenone

(S)-2-phenyl-butan-2-ol
53777-08-5

(S)-2-phenyl-butan-2-ol

Conditions
Conditions Yield
diethylzinc; acetophenone; With (S)-N-(3-methyl-1-(1-pyrrolidin-1-yl)butan-2-yl)-P,P-di(naphthalen-1-yl)phosphinic amideamine; at 20 ℃; for 8h; Inert atmosphere; Neat (no solvent);
With ammonium chloride; In diethyl ether; water; at 0 ℃; optical yield given as %ee; enantioselective reaction; Inert atmosphere;
89%
With titanium(IV) isopropylate; (1R,2R)-N,N'-bis<(1S,4R)-7,7-dimethyl-2-oxo-bicyclo<2.2.1>heptylmethanesulfonyl>-1,2-cyclohexyldiamine; In toluene; at 25 ℃; for 8h;
80%
diethylzinc; acetophenone; (S)-N-(3-methyl-1-(1-pyrrolidin-1-yl)butan-2-yl)-P,P-di(naphthalen-1-yl)phosphinic amideamine; In n-heptane; at 20 ℃; for 24.5h; Inert atmosphere;
With ammonium chloride; In n-heptane; water; at 0 ℃; Product distribution / selectivity;
80%
With titanium(IV) isopropylate; In hexane; toluene; at 10 ℃; for 50h;
75%
With titanium(IV) isopropylate; 1R,2R-[(1S,2R,4R-2-OH-7,7-Me2-bicycloheptyl)CH2SO2NH]2C6H10; In hexane; toluene; at 20 ℃; for 29h;
71%
With titanium(IV) isopropylate; trans-(R,R)-1,2-cyclohexane-bis(sulfonamide) ligand 6; In toluene; at 20 ℃; for 29h;
71%
diethylzinc; With titanium(IV) isopropylate; bicyclo[2.2.1]heptane-1-methanesulfonamide,N,N'-(1S,2S)-1,2-cyclohexanediylbis[2-hydroxy-7,7-dimethyl]-(1R,1'R,2S,2'S,4S,4'S)-(9CI); In toluene; at 20 ℃; for 0.0833333 - 0.166667h;
acetophenone; In toluene; at 20 ℃;
With ammonium chloride; In water; toluene; Product distribution / selectivity;
71%
titanium(IV) isopropylate; L-tartaric acid-based sulfonamide ligand; In hexane; toluene; at 20 ℃; for 40h;
70%
With titanium(IV) isopropylate; 1-(p-MeOC6H4SO2NH)-2-(isoborneolsulfonylamino)cyclohexane; In toluene; at 25 ℃; for 120h;
65%
titanium(IV) isopropylate; [(R,R)-2-(isoborneol-10-SO2NH)cyclohexylsulfamoyl]-polymer; In toluene; at 25 ℃; for 408h;
56%
diethylzinc; acetophenone; With titanium(IV) isopropylate; C36H48N2O6S2; In toluene; at 25 ℃; for 24h; Inert atmosphere;
With water; In toluene; optical yield given as %ee; enantioselective reaction;
50%
With titanium(IV) isopropylate; In toluene; at 25 ℃; for 120h; optical yield given as %ee; enantioselective reaction;
40%
With titanium(IV) isopropylate; (R,R)-C6H4-bis((1S)-camphosulfonylamide); In hexane; at 20 ℃;
dimethyl zinc(II)
544-97-8

dimethyl zinc(II)

1-phenyl-propan-1-one
93-55-0

1-phenyl-propan-1-one

(S)-2-phenyl-butan-2-ol
53777-08-5

(S)-2-phenyl-butan-2-ol

(R)-2-phenyl-butan-2-ol
1006-06-0

(R)-2-phenyl-butan-2-ol

Conditions
Conditions Yield
With titanium(IV) isopropylate; calcium hydride; (1S,2R,4S)-N-(naphth-1-ylmethyl)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>hept-1-ylmethanesulfonamide; In toluene; at 4 ℃; for 336h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With titanium(IV) isopropylate; chiral camphorsulfonamide derivative (1b, R1=OH, R2=H, R3=1-naphthylmethyl); In toluene; at 4 ℃; for 336h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With titanium(IV) isopropylate; (1S,2R,4S,1'S,2'R,4'S)-C28H44N2O6S2 (m-substituted benzene); In toluene; at 25 ℃; for 3h; Title compound not separated from byproducts;
With titanium(IV) isopropylate; 1R,2R-[(1S,2R,4R-2-OH-7,7-Me2-bicycloheptyl)CH2SO2NH]2C6H10; In hexane; toluene; at 20 ℃; for 45h; Title compound not separated from byproducts;
With titanium(IV) isopropylate; (R,R)-bissulfonamide diol ligand; at 20 ℃; for 72h; Title compound not separated from byproducts;
With titanium(IV) isopropylate; trans-(R,R)-1,2-cyclohexane-bis(sulfonamide) ligand; In hexane; toluene; at 20 ℃; Title compound not separated from byproducts.;
methylmagnesium bromide
75-16-1

methylmagnesium bromide

1-phenyl-propan-1-one
93-55-0

1-phenyl-propan-1-one

(S)-2-phenyl-butan-2-ol
53777-08-5

(S)-2-phenyl-butan-2-ol

Conditions
Conditions Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 2,4-di-tert-butyl-6-({[(1R,2R)-2-(dimethylamino)cyclohexyl](methyl)amino}methyl)phenol; at -78 ℃;
61%
diethylzinc
557-20-0

diethylzinc

acetophenone
98-86-2

acetophenone

(S)-2-phenyl-butan-2-ol
53777-08-5

(S)-2-phenyl-butan-2-ol

(R)-2-phenyl-butan-2-ol
1006-06-0

(R)-2-phenyl-butan-2-ol

Conditions
Conditions Yield
With titanium(IV) isopropylate; calcium hydride; (1S,2R,4S)-N-(naphth-1-ylmethyl)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>hept-1-ylmethanesulfonamide; In toluene; at 4 ℃; for 96h; Product distribution; enantioselective addition; other chiral ligand, solvent, time, salt effect, other ketones.;
With titanium(IV) isopropylate; In toluene; at 25 ℃; for 24h; Product distribution; different ketones, dialkylzinc reactants, chiral camphorsulfonamides and reaction conditions;
With titanium(IV) isopropylate; chiral camphorsulfonamide derivative (1a, R1=OH, R2=H, R3=benzyl); In toluene; at 25 ℃; for 24h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With titanium(IV) isopropylate; (1S,2R,4S,1'S,2'R,4'S)-C28H44N2O6S2 (m-substituted benzene); In toluene; at 25 ℃; for 2h; Further Variations:; Reagents; Temperatures; Product distribution;
With titanium(IV) isopropylate; (1S,2S)-1,2-diaminocyclopentane bis(sulfonamide) diol; In toluene; at 20 ℃; Title compound not separated from byproducts;
With poly(BINOL-BINAP)-ruthenium; In toluene; at 0 ℃; for 5.5h; Title compound not separated from byproducts.;
With titanium(IV) isopropylate; In toluene; at 25 ℃; for 3h; Further Variations:; Reagents; Temperatures; time; Product distribution;
diethylzinc; With chiral di(naphthalen-1-yl)phosphinic amide-based reagent; In pentane; at -78 ℃; for 0.5h;
acetophenone; In pentane; at 20 ℃; for 24h; Further stages. Title compound not separated from byproducts.;
With titanium(IV) isopropylate; In toluene; at 25 ℃; for 96h; Title compound not separated from byproducts.;
diethylzinc; acetophenone; With titanium(IV) isopropylate; C36H48N2O6S2; In toluene; at 25 ℃; for 24h; Inert atmosphere;
With water; In toluene; optical yield given as %ee; enantioselective reaction;
With (S)-N-(3-methyl-1-(1-pyrrolidin-1-yl)butan-2-yl) diphenylphosphinic amideamine; In n-heptane; at 20 ℃; for 24h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;
With [(1R,2R)-2-[(diphenylphosphoroso)amino]-1,2-diphenylethyl](pentyl)amine; In toluene; at 0 - 20 ℃; for 24h; Reagent/catalyst; enantioselective reaction; Inert atmosphere; Schlenk technique;
87 % ee
ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

acetophenone
98-86-2

acetophenone

(S)-2-phenyl-butan-2-ol
53777-08-5

(S)-2-phenyl-butan-2-ol

(R)-2-phenyl-butan-2-ol
1006-06-0

(R)-2-phenyl-butan-2-ol

Conditions
Conditions Yield
chiral podand crown ether; In toluene; for 24h; Further Variations:; Catalysts; Product distribution;
With 2,4-di-tert-butyl-6-({[(1R,2R)-2-(dimethylamino)cyclohexyl](methyl)amino}methyl)phenol; In diethyl ether; toluene; at -78 ℃; for 1.5h; Reagent/catalyst; Solvent; Time; Temperature; Overall yield = 77 %; Overall yield = 11.5 mg;
80 % ee
acetophenone; With 2,4-di-tert-butyl-6-({[(1R,2R)-2-(dimethylamino)cyclohexyl](methyl)amino}methyl)phenol; In toluene; at 20 ℃; for 0.0833333h; Schlenk technique;
ethylmagnesium bromide; In diethyl ether; toluene; at -78 ℃; enantioselective reaction; Schlenk technique;
78 % ee
With 2,4-di-tert-butyl-6-({[(1R,2R)-2-(dimethylamino)cyclohexyl](methyl)amino}methyl)phenol; In toluene; at -78 ℃; enantioselective reaction;
78 % ee
With {2-[(3,5-di-tert-butyl-2-hydroxy-benzyl)-methyl-amino]-cyclohexyl}-carbamic acid tert-butyl ester; In diethyl ether; toluene; at -82 ℃; for 0.333333h; Reagent/catalyst; enantioselective reaction; Schlenk technique; Inert atmosphere;
70% ee
With 2,4-di-tert-butyl-6-({[(1R,2R)-2-(dimethylamino)cyclohexyl](methyl)amino}methyl)phenol; In diethyl ether; toluene; at -82 ℃; for 0.333333h; Reagent/catalyst; enantioselective reaction; Schlenk technique; Inert atmosphere;
76% ee
methylmagnesium bromide
75-16-1

methylmagnesium bromide

(R)-2-methyl-2-phenyloxirane
2085-88-3,2404-43-5,21019-52-3,100018-61-9

(R)-2-methyl-2-phenyloxirane

(S)-2-phenyl-butan-2-ol
53777-08-5

(S)-2-phenyl-butan-2-ol

Conditions
Conditions Yield
With copper(l) iodide; In tetrahydrofuran;
86%
With copper(l) iodide;
43%
[2R,(S)R]-2-phenyl-3-p-tolylsulfinylbutan-2-ol

[2R,(S)R]-2-phenyl-3-p-tolylsulfinylbutan-2-ol

(S)-2-phenyl-butan-2-ol
53777-08-5

(S)-2-phenyl-butan-2-ol

Conditions
Conditions Yield
nickel; In ethanol; at 20 ℃; for 24h;
65%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

1-phenyl-propan-1-one
93-55-0

1-phenyl-propan-1-one

(S)-2-phenyl-butan-2-ol
53777-08-5

(S)-2-phenyl-butan-2-ol

(R)-2-phenyl-butan-2-ol
1006-06-0

(R)-2-phenyl-butan-2-ol

Conditions
Conditions Yield
With 2,4-di-tert-butyl-6-({[(1R,2R)-2-(dimethylamino)cyclohexyl](methyl)amino}methyl)phenol; at -78 ℃; Overall yield = 75 %;
88 % ee
With C28H44N2O; In diethyl ether; toluene; at -82 ℃; for 0.583333h; Reagent/catalyst; Overall yield = 46 percentChromat.; enantioselective reaction; Schlenk technique; Inert atmosphere;
74% ee

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