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Syntheses of Cyclopropyl Silyl Ketones

 

作者: Markus E. Scheller,   Bruno Frei,  

 

期刊: Helvetica Chimica Acta  (WILEY Available online 1986)
卷期: Volume 69, issue 1  

页码: 44-52

 

ISSN:0018-019X

 

年代: 1986

 

DOI:10.1002/hlca.19860690107

 

出版商: WILEY‐VCH Verlag GmbH

 

数据来源: WILEY

 

摘要:

AbstractThe synthesis of the cyclopropyl silyl ketones1–4is described. The trimethylsilyl ketone1was prepared from geraniol ((E)‐5) inca.10% overall yield by cyclopropanation leading to6, CrO3oxidation to the aldehyde8, reaction of the latter with trimethylsilyl anion to14A+B, and CrO3oxidation to1. Also for the (t‐butyl)dimethylsilyl ketones2–4, an efficient four‐step synthesis with overall yields of 48%, 85%, and 13%, respectively, was elaborated, starting from the allylic alcohols (E)‐5, and23. The method of preparation involves as the key step aWittigrearrangement of the silylallyl ethers ((E/Z)‐20,24) to the silyl alcohols ((E/Z)‐21,25), subsequent cyclopropanation (19A+B,22A+B,26), and oxidation to the cyclopropyl s

 

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