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面包酵母介导的2-烯丙基-2-乙氧羰基环戊酮的对映面选择性还原反应

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

作者信息

Fraga C A, Barreiro E J

机构信息

Laboratório de Avaliação e Síntese de Substâncias Bioativas (LASSBio), Faculdade de Farmácia, Universidade Federal do Rio de Janeiro, Brazil.

出版信息

Chirality. 1996;8(4):305-10. doi: 10.1002/(SICI)1520-636X(1996)8:4<305::AID-CHIR3>3.0.CO;2-E.

DOI:10.1002/(SICI)1520-636X(1996)8:4<305::AID-CHIR3>3.0.CO;2-E
PMID:8789834
Abstract

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-2-carboethoxy-cyclopentanol derivative (6). This methodology also provides an entry to corresponding beta-keto ester (-)-(2), representing an important strategy to prepare chiral functionalized 2-oxabicyclic[3.3.0]octane and 2-oxabicyclic[4.4.0]nonane derivatives, useful synthons to access new bioactive compounds.

摘要

在氧化铜存在的情况下，使用面包酵母以高对映体过量（>99%）完成了2-烯丙基-2-乙氧羰基环戊酮（2）的对映选择性还原，得到（+）-2-烯丙基-2-乙氧羰基环戊醇衍生物（6）。该方法还提供了制备相应的β-酮酯（-）-（2）的途径，这是制备手性官能化的2-氧杂双环[3.3.0]辛烷和2-氧杂双环[4.4.0]壬烷衍生物的重要策略，这些衍生物是合成新的生物活性化合物的有用合成子。

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