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Synthesis of 2,3,4-Trisubstituted Thiochromanes using an Organocatalytic Enantioselective Tandem Michael–Henry Reaction

Authors
  • Dodda, Rajasekhar
  • Goldman, Joshua J.
  • Mandal, Tanmay
  • Zhao, Cong-Gui
  • Broker, Grant A.
  • Tiekink, Edward R. T.
Type
Published Article
Journal
Advanced Synthesis & Catalysis
Publisher
Wiley (John Wiley & Sons)
Publication Date
Feb 26, 2008
Volume
350
Issue
4
Pages
537–541
Identifiers
DOI: 10.1002/adsc.200700331
PMID: 19829750
PMCID: PMC2760986
Source
PubMed Central
Keywords
License
Unknown

Abstract

Enantioenriched 2,3,4-trisubstituted thiochromanes have been synthesized by using a cupreine-catalyzed tandem Michael addition–Henry reaction between 2-mercaptobenzaldehydes and β-nitrostyrenes. Good diastereoselectivities and enantioselectivities were obtained for the title compounds, which may be further improved through a single recrystallization (up to 98% de and> 99% ee ).

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