Direct catalytic asymmetric vinylogous mannich-type reaction of γ-butenolides with ketimines

Liang Yin, Hisashi Takada, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

62 Citations (Scopus)

Abstract

A cooperative catalyst consisting of a soft Lewis acid and a hard Brønsted base promoted the title reaction. The N-thiophosphinoyl group on the ketimines was critical to surpass the high activation barrier through the soft-soft interaction of sulfur and copper. Mannich adducts with a tetrasubstituted stereogenic center were produced with excellent diastereo- and enantioselectivities. TANIAPHOS= ferrocenyl ligand.

Original languageEnglish
Pages (from-to)7310-7313
Number of pages4
JournalAngewandte Chemie - International Edition
Volume52
Issue number28
DOIs
Publication statusPublished - 2013 Jul 8
Externally publishedYes

Keywords

  • asymmetric catalysis
  • atom economy
  • cooperative catalysis
  • ketimines
  • synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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