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ID 195
file
creator
Sakurama, Keiki
Yoshii, Eiichi
subject
vinylcyclopropane-cyclopentene
low temperature
2-(2-(trimethylsilyl)ethenyl)cyclopropyl
NDC
Chemistry
abstract
Reactions of four diastereomeric 2-(2-(trimethylsilyl)ethenyl)cyclopropyl acetates 7, derived from enol silyl ether 4 and Fischer carbene complex 6, with 2.2 equiv of MeLi at -80 ° to -30 °C afforded cyclopentenol 8 as a single diastereomer and acyclic enol silyl ethers 9 via the corresponding cyclopropanolates in ratios depending on the vinylsilane geometry. Predominant formation of 8 over 9 from (Z)-7 irrespective of the stereochemistry at C-1 was observed. This is the first example of oxyanion-accelerated vinylcyclopropane-cyclopentene rearrangement which proceeds at unprecedentedly low temperatures.
journal title
Tetrahedron letters
volume
Volume 38
issue
Issue 18
start page
3257
end page
3260
date of issued
1997-05-05
publisher
Elsevier Science Ltd.
issn
0040-4039
language
eng
nii type
Journal Article
HU type
Journal Articles
DCMI type
text
format
application/pdf
text version
author
rights
Copyright (c) 1997 Elsevier Science Ltd.
relation is version of URL
http://dx.doi.org/10.1016/S0040-4039(97)00579-0
department
Graduate School of Biomedical Science