Acetophenone → 1-Phenylethanol, (S)-

HRID 2289178Notes

Reaction equation

HRID 2289178 reaction equation
C1([C@@H](N)C)C=CC=CC=1.[C:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:12])[CH3:11].C1([C@H](O)C)C=CC=CC=1>COCCOCCOC>[C:13]1([C@@H:10]([OH:12])[CH3:11])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7410Acetophenone2×HCID 758181-Phenethylamine, (-)-2×HCID 6375161-Phenylethanol, (R)-

Product 1

HCID 4431351-Phenylethanol, (S)-

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

It is to be understood that for a particular chiral hydride complex, the chiral ligand thereof will produce an enantiomeric excess of a reduction product such that for that particular hydride complex, the use of the same chiral ligand but of the opposite enantiomer will give rise to the reduction product of the opposite stereochemistry. For example, whereas NaAlH2 ((+)-DDM) reduces acetophenone to (R)-1-phenylethan-1-ol in 91% enantiomeric excess (0° C.; 48 h; diglyme), reduction of acetophenone with NaAlH2 ((-)-DDM) under identical conditions will give an enantiomeric excess of (S)-1-phenylethan-1-ol.

Workup

  1. customthe chiral ligand thereof will produce an enantiomeric excess of a reduction product such that for that particular hydride complex
  2. customthe use of the same chiral ligand but of the opposite enantiomer will give rise to the reduction product of the opposite stereochemistry

Sources & evidence

ORD record
ord-389973a6e509450aa893d5882a31a954
Source dataset
uspto-grants-2000_07
Patent number
US06090950

Reaction notes

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