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Asymmetric reduction of Z-3-chloro-3-alken-2-ones with fermenting baker's yeast

✍ Scribed by Masanori Utaka; Satoshi Konishi; Akira Takeda

Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
254 KB
Volume
27
Category
Article
ISSN
0040-4039

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✦ Synopsis

Using fermenting baker's yeast, Z-RCH=CClCOCH3 (R=C2HS, n-C5Hll, n-CaH17)

was reduced initially to (S)-RCH2EHClCOCH3 in 44-84% ee, which was further reduced to RCH2?HCltHOHCH3 in >98% ee with the syn(2S,3S)/anti(2S,3R) ratios of 2.6-18.3. The use of fermenting baker's yeast has been shown to provide a versatile chiral reducing agent in organic synthesis.

1 Various prochiral compounds such as S-keto esters 2 and a,S-unsaturated ketones 3 have been studied rather exten-

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