Enantioselektive Verseifung der Diacetate von 2‐Nitro‐1,3‐diolen mit Schweineleber‐Esterase und Herstellung enantiomerenreiner Derivate von 2‐Nitro‐allylalkoholen (chirale Verknüpfungsreagenzien)
作者:
Martin Eberle,
Martin Egli,
Dieter Seebach,
期刊:
Helvetica Chimica Acta
(WILEY Available online 1988)
卷期:
Volume 71,
issue 1
页码: 1-23
ISSN:0018-019X
年代: 1988
DOI:10.1002/hlca.19880710102
出版商: WILEY‐VCH Verlag GmbH
数据来源: WILEY
摘要:
Enantioselective Saponification of Diacetates of 2‐Nitro‐1,3‐propanediols by Pig‐Liver Esterase and Preparation of Enantiomerically Pure Derivatives of 2‐Nitro‐allylic Alcohols (Chiral Multiple‐Coupling Reagents)The reproducible enantioselective saponification of open‐chain and cyclic diacetates ofmeso‐2‐nitro‐1,3‐propanediols (see4b–13b) with pig‐liver esterase (PLE) gives monoacetates (see4c–l3c) of>95% enantiomeric excess. TheReenantiotopic acetate group appears to be saponified preferentially, as proved by the X‐ray crystal structure analysis of three camphanoates4d,6d, and7d. Elimination of H2O or AcOH from the hydroxy acetates thus available gives derivatives of nitro‐allylic alcohols (see20–24,27, and29) which are subjected to diastereoselectiveMi
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