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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