[4+2] Cycloadditions of 2-(trialkylsilyloxy)-allylidenecyclopropanes - synthesis of spiro[2.5]octan-5-ones

Thies Thiemann, Stephan Kohlstruk, Gerhard Schwär, Armin de Meijere

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

The previously unknown 2-(trialkylsilyloxy)allylidenecyclopropanes 2a-d have been prepared by silyl-enolization of the easily available cyclopropylidenealkanones 1-R1 in good yields. Dienes 2a-d readily react with a variety of dienophiles at temperatures ranging from 0 to 130°C to give derivatives 5-10 of 5-(trialkylsilyloxy)spiro-[2.5]oct-4-ene or the corresponding hydrolysis products 10, 12. Weak dienophiles like cyclohexenone and cyclopentenone give spiro[2.5]octan-5-one derivatives only under BF3 catalysis and with poor yields.

Original languageEnglish
Pages (from-to)3483-3486
Number of pages4
JournalTetrahedron Letters
Volume32
Issue number29
DOIs
Publication statusPublished - Jul 15 1991
Externally publishedYes

Keywords

  • BF catalysis
  • Diels-Alder reactions
  • Ring strain and donor activated dienes
  • spirocyclopropane mimic of gem-dimethyl groups

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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