Intramolecular Michael-type additions to vinyl bissulfoxides: Enantioselective synthesis of chiral aldehydes

Timo Gehring, Joachim Podlech*, Alexander Rothenberger

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

The diastereoselective auxiliary-based intramolecular Michael-type additions to alkylidene bissulfoxides derived from dithiane and dithiolane were investigated. Utilization of substrates bearing N- and O-nucleophilic functions led to the formation of the respective cyclic substrates with selectivities ranging from 51:49 to 85:15. Cleavage of the bissulfoxide moiety by a two-step sequence yielded chiral carbaldehydes. The enantiomerically pure compounds obtained by this procedure, for example, tetrahydropyran-2-carbaldehyde and homopipecolic aldehyde, are hardly accessible by other routes. Both enantiomers of the target molecules are available since the stereochemical information is introduced with the readily available diethyl D- and L-tartrates.

Original languageEnglish (US)
Article numberE22108SS
Pages (from-to)2476-2487
Number of pages12
JournalSynthesis
Issue number15
DOIs
StatePublished - Aug 1 2008

Keywords

  • Nucleophilic additions
  • Stereoelectronic effects
  • Sulfoxides
  • Thioacetals
  • Umpolung

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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