Direct Catalytic Asymmetric Mannich-type Reaction of α,β-Unsaturated γ-Butyrolactam with Ketimines

Shaoquan Lin, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

18 Citations (Scopus)

Abstract

We report a direct catalytic asymmetric Mannich-type addition of α,β-unsaturated γ-butyrolactam to α-ethoxycarbonyl ketimines promoted by a soft Lewis acid/Brønsted base cooperative catalyst. A thiophosphinoyl group on the nitrogen of ketimines was crucial for both electrophilic activation and α-addition of γ-butyrolactams. The obtained aza-Morita-Baylis-Hillman-type products bear an α-amino acid architecture with a tetra-substituted stereogenic center. Ambident nucleophile! A direct catalytic asymmetric Mannich-type addition of α,β-unsaturated γ-butyrolactam to α-ethoxycarbonyl ketimines promoted by a soft Lewis acid/Brønsted base cooperative catalyst has been developed (see scheme; Ph-BPE=1,2-bis(2,5-dimethylphospholano)ethane). The obtained aza-Morita-Baylis-Hillman-type products bear an α-amino acid architecture with a tetra-substituted stereogenic center.

Original languageEnglish
Pages (from-to)3296-3299
Number of pages4
JournalChemistry - A European Journal
Volume22
Issue number10
DOIs
Publication statusPublished - 2016 Mar 1
Externally publishedYes

Keywords

  • amino acids
  • asymmetric catalysis
  • cooperative effects
  • ketimines
  • lactams

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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