Lewis base catalysis of the Mukaiyama directed aldol reaction: 40years of inspiration and advances

Gregory L. Beutner, Scott E. Denmark

Research output: Contribution to journalReview article

Abstract

Since the landmark publications of the first directed aldol addition reaction in 1973, the site, diastereo-, and enantioselective aldol reaction has been elevated to the rarefied status of being both a named and a strategy-level reaction (the Mukaiyama directed aldol reaction). The importance of this reaction in the stereoselective synthesis of untold numbers of organic compounds, both natural and unnatural, cannot be overstated. However, its impact on the field extends beyond the impressive applications in synthesis. The directed aldol reaction has served as a fertile proving ground for new concepts and new methods for stereocontrol and catalysis. This Minireview provides a case history of how the challenges of merging site selectivity, diastereoselectivity, enantioselectivity, and catalysis into a unified reaction manifold stimulated the development of Lewis base catalyzed aldol addition reactions. The evolution of this process is chronicled from the authors' laboratories as well as in those of Professor Teruaki Mukaiyama.

Original languageEnglish (US)
Pages (from-to)9086-9096
Number of pages11
JournalAngewandte Chemie - International Edition
Volume52
Issue number35
DOIs
StatePublished - Aug 26 2013

Keywords

  • Lewis bases
  • aldol reaction
  • diastereoselectivity
  • enantioselectivity
  • silanes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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