1,4-Additions of the highly functionalized copper reagents RCu(CN)ZnI · 2 BFP3 to trisubstituted enones. A new BF3 promoted cyclization reaction

Ming Chang P. Yeh, Paul Knochel, William M. Butler, Scott C. Berk

Research output: Contribution to journalArticle

50 Citations (Scopus)

Abstract

The new copper reagents RCu(CN)Zn I · 2 BF3 1 containing various functional groups like esters, cyanides, chlorides or enoates react with β, β′- disubstituted enones to afford the Michael adducts 4-7 in high yields (81-98%). Cyano-substituted 1,4-adducts undergo a new cyclization reaction leading to the very stable bicyclic difluoroboron enolates 11a-11c which could be converted into the bicyclic diketones 12 under mild basic conditions. The X-ray structure of 11b is reported.

Original languageEnglish
Pages (from-to)6693-6696
Number of pages4
JournalTetrahedron Letters
Volume29
Issue number51
DOIs
Publication statusPublished - 1988

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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