(+)-1(S), 5(R), 8(S)-8-phenyl-2-azabicyclo[3.3.0]octan-8-ol n,o-methylboronate (2) and its enantiomer, chiral chemzymes which serve as catalysts for their own enantioselective synthesis

✍ Scribed by E.J Corey; C.-P Chen; Gregory A Reichard

• Publisher: Elsevier Science
• Year: 1989
• Tongue: French
• Weight: 304 KB
• Volume: 30
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)93796-7

✦ Synopsis

An efficient synthesis of (+)-l(S), 5(R), 8(S)-8-phenyl-2-azabicyclo[3.3.0]octan-S-o1 (1) and its enantiomer is described.

The B-methyloxazaborolidine derivatives (2) of these amino alcohols are excellent catalysts (chemzymes)

for the enantioselective reduction of a variety of achiral ketones to chiral secondary alcohols, e.g. acetophenone, 98% ee; pinacolone, 98% ee; a-tetralone, 97% ee; and 2-bromo-2-cyclohexen-lone, 98% ee. The oxazaborolidine 2 is a catalyst for the enantioselective synthesis of 14, a starting material for the synthesis of chiral 2 itself.