Enantioselective organocatalytic direct aldol reactions of α-oxyaldehydes: Step one in a two-step synthesis of carbohydrates

Alan B. Northrup, Ian K. Mangion, Frank Hettche, David W.C. MacMillan

Research output: Contribution to journalArticle

296 Scopus citations

Abstract

Two-faced: α-Oxyaldehydes can act as both an aldol donor and an aldol acceptor and can be coupled enantioselectively by using proline as the reaction catalyst. This new aldol reaction provides an operationally simple protocol for the stereo-controlled production of erythrose (see scheme) architecture and sets the stage for a two-step enantioselective synthesis of carbohydrates.

Original languageEnglish (US)
Pages (from-to)2152-2154
Number of pages3
JournalAngewandte Chemie - International Edition
Volume43
Issue number16
DOIs
StatePublished - Apr 13 2004

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Keywords

  • Aldehydes
  • Aldol reaction
  • Carbohydrates
  • Enantioselectivity
  • Homogeneous catalysis

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