Main > PHARMA. > Asymmetric Synthesis > Hydroxy-4-Phenylbutanenitrile > (S)-2-Hydroxy-4-Ph butanenitrile

Product Japan. U

CORP. SALE Catalyst structure:
Based on single-isomer binaphthol that also has diphenylphosphine oxide groups at the 3-positions of both naphthalene rings. The researcher completes the synthesis of the catalyst by reaction of that binaphthol with Al chloride so that the 2 O atoms bind to an Al-Cl Lewis acid group
SYNTHESIS In a reaction of
- Trimethylsilyl cyanide with
- Beta-phenylpropionaldehyde
the Al Lewis acid activates the aldehyde carbonyl group while the diphenylphosphine oxide Lewis base groups activate the cyanide nucleophile. The result is
- (S)-2-Hydroxy-4-phenylbutanenitrile in 97% yield & 97% ee
UPDATE 10.99
AUTHOR Shibasaki Masakatsu; Pharmacy Prof
LITERATURE REF. J. Am. Chem. Soc., 121, p. 2641 (1999)

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