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Enantiofacial selective reduction of 2-allyl-2-carboethoxy-cyclopentanone mediated by baker's yeast

✍ Scribed by Carlos A. M. Fraga; Eliezer J. Barreiro

Publisher: John Wiley and Sons
Year: 1996
Tongue: English
Weight: 423 KB
Volume: 8
Category: Article
ISSN: 0899-0042
DOI: 10.1002/(sici)1520-636x(1996)8:4<305::aid-chir3>3.0.co;2-e

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✦ Synopsis

Enantioselective reduction of 2-allyl-2-carboethoxy-cyclopentanone (2) was accomplished in high enantiomeric excess (> 99%), using baker's yeast in the presence of CuO, to obtain the (+)-2-allyl-2carboethoxycyclopentanol derivative (6). This methodology also provides an entry to corresponding p-keto ester (-)-( 2), representing an important strategy to prepare chiral functionalized 2-oxabicyclic i3.3.01 octane and 2-oxabicyclic[4.4.0lnonane derivatives, useful synthons to access new bioactive compounds. o 1996 Wiley-Liss, Inc.

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