Transition Metal Catalyzed Intramolecular Cyclizations of (Trichloromethyl)alkenes

Gary M. Lee, Steven M. Weinreb

Research output: Contribution to journalArticlepeer-review

76 Scopus citations

Abstract

Intramolecular Kharasch cyclizations of a variety of functionalized olefinic trichloromethyl substrates are promoted by transition-metal complexes. The regioselectivity of the cyclization is critically dependent upon the structure of the trichloromethyl compound. Thus, trichloromethyl substrate 1 afforded primarily five-membered ring exo closure product 8, as did 5a and 6, yielding mainly trichloro alcohol 12. Similarly trichloroalkene 2 gave primarily the six-membered ring exo closure product 10. Trichloromethyl ketones 7a-e, on the other hand, produced predominantly endo closure products.

Original languageEnglish (US)
Pages (from-to)1281-1285
Number of pages5
JournalJournal of Organic Chemistry
Volume55
Issue number4
DOIs
StatePublished - Jan 1 1990

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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