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

Shaoquan Lin, Naoya Kumagai, Masakatsu Shibasaki

研究成果: Article査読

26 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)3296-3299
ページ数4
ジャーナルChemistry - A European Journal
22
10
DOI
出版ステータスPublished - 2016 3月 1
外部発表はい

ASJC Scopus subject areas

  • 化学一般
  • 触媒
  • 有機化学

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