Rationalization of an Unusual Solvent-Induced Inversion of Enantiomeric Excess in Organocatalytic Selenylation of Aldehydes

Research output: Contribution to journalArticle

  • Authors:
  • Jordi Bures
  • Paul Dingwall
  • Alan Armstrong
  • Donna G. Blackmond

Abstract

An unusual solvent-induced inversion of the sense of enantioselectivity obsd. in the α-selenylation of aldehydes catalyzed by a diphenylprolinol silyl ether catalyst is correlated to the presence of intermediates formed subsequent to the highly selective C-Se bond-forming step in the catalytic cycle. This work provides support for a mechanistic concept for enamine catalysis and includes a general role for "downstream intermediates" in selectivity outcomes in organocatalysis. [on SciFinder(R)]

Bibliographical metadata

Original languageEnglish
Pages (from-to)8700-8704
Number of pages5
JournalAngew. Chem., Int. Ed.
Volume53
DOIs
Publication statusPublished - 2014

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