Mechanistic rationalization of organocatalyzed conjugate addition of linear aldehydes to nitro-olefins

Research output: Contribution to journalArticle

  • Authors:
  • J. Bures
  • A. Armstrong
  • D. G. Blackmond

Abstract

Kinetic studies of the conjugate addition of propanal to nitrostyrene catalyzed by diarylprolinol ethers reveal that formation of the product iminium species is rate-determining and is promoted by both the reaction product and acid additives. The beneficial role of a dominant cyclobutane intermediate in maintaining high stereoselectivity is highlighted. This mechanistic understanding led to the design of highly productive reaction protocols.

Bibliographical metadata

Original languageEnglish
Pages (from-to)8822-8825
Number of pages4
JournalJ Am Chem Soc
Volume133
DOIs
Publication statusPublished - 2011