Vinylcyclopropane oxygenation. Anti diastereoselectivity through an unexpected transition-state geometry

Ken S. Feldman, Carolyn M. Kraebel

Research output: Contribution to journalArticlepeer-review

25 Scopus citations

Abstract

Ester-substituted vinylcyclopropanes react with molecular oxygen via a radical-mediated [3-atom + 2-atom] addition to form 1,2-dioxolanes with predominantly anti stereochemistry. The degree of anti stereoselectivity can be controlled by the electronic nature of the radical stabilizing substituent R.

Original languageEnglish (US)
Pages (from-to)4574-4576
Number of pages3
JournalJournal of Organic Chemistry
Volume57
Issue number17
StatePublished - 1992

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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