Stereoselective conjugate addition of ketones to alkylidene malonates using thiourea-sulfonamide organocatalyst

Masahiro Kawada, Kosuke Nakashima, Shin ichi Hirashima, Toru Sakagami, Yuji Koseki, Tsuyoshi Miura

Research output: Contribution to journalArticlepeer-review

Abstract

In this study, stereoselective conjugate addition of ketones to alkylidene malonates using organocatalyst has been developed. The reaction in the presence of 20 mol% of a novel thiourea-sulfonamide organocatalyst afforded conjugate adducts in moderate to high yields (up to 81%) under mild reaction conditions. Excellent diastereoselectivity (up to 98:2 dr) and enantioselectivity (up to 88% ee) were achieved.

Original languageEnglish
Pages (from-to)1215-1224
Number of pages10
JournalChirality
Volume30
Issue number11
DOIs
Publication statusPublished - 2018 Nov
Externally publishedYes

Keywords

  • alkylidene malonate
  • asymmetric conjugate addition
  • organocatalysis
  • organocatalyst
  • thiourea-sulfonamideIntroduction

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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