Asymmetric organocatalytic domino Michael/aldol reactions: Enantioselective synthesis of chiral cycloheptanones, tetrahydrochromenones, and polyfunctionalized bicyclo-[3.2.1]octanes

Magnus Rueping*, Alexander Kuenkel, Francisco Tato, Jan W. Bats

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

139 Scopus citations

Abstract

C! mon 1,2-dione: A new diastereo- and enantioselective Lewis base catalyzed domino Michael/aldol reaction converts α, β-unsaturated aldehydes and 1,2-diones into chiral bicyclo[3.2.1]octane-6- carbaldehydes. The products are produced in good to excellent enantioselectivities (90- 98 % ee) and can be transformed into bicyclic diols and triols. Additionally, a retroaldol cyclization provides access to valuable tetrahydrochromenones (see scheme).

Original languageEnglish (US)
Pages (from-to)3699-3702
Number of pages4
JournalAngewandte Chemie - International Edition
Volume48
Issue number20
DOIs
StatePublished - May 4 2009
Externally publishedYes

Keywords

  • Aldol reaction
  • Domino reaction
  • Michael addition
  • Organocatalysis
  • Prolinol ethers

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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