Carboalumination of Seven-Membered-Ring trans-Alkenes

Margaret A. Greene, Yudong Liu, Jillian R. Sanzone, K. A. Woerpel

Research output: Contribution to journalArticlepeer-review

Abstract

Seven-membered-ring trans-alkenes undergo rapid hydro- and carboalumination reactions in the absence of a catalyst with complete regio- and diastereoselectivity. Control experiments, including deuterium labeling, adding radical inhibitors, and using a radical clock, suggest that these reactions proceed by a concerted mechanism. The products of the reaction possess a new carbon-aluminum bond that can then undergo subsequent transformations, particularly oxidation, providing functionalized products as single stereoisomers.

Original languageEnglish (US)
Pages (from-to)7518-7521
Number of pages4
JournalOrganic Letters
Volume22
Issue number19
DOIs
StatePublished - Oct 2 2020

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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