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Low-temperature oxyanion-accelerated vinylcyclopropane-cyclopentene rearrangement. Reaction of 2-(2-(trimethylsilyl)-ethenyl)cyclopropyl acetates with methyl lithium

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Keywords
  • Vinylcyclopropane-Cyclopentene
  • Low Temperature
  • 2-(2-(Trimethylsilyl)Ethenyl)Cyclopropyl
  • Ndc:430
Disciplines
  • Chemistry
  • Mathematics

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.

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