Catalytic asymmetric phase-transfer michael reaction and Mannich-type reaction of glycine schiff bases with tartrate-derived diammonium salts

Tomoyuki Shibuguchi, Hisashi Mihara, Akiyoshi Kuramochi, Takashi Ohshima, Masakatsu Shibasaki

Research output: Contribution to journalReview article

69 Citations (Scopus)

Abstract

Catalytic asymmetric Michael and Mannich-type reactions of glycine Schiff hases with chiral two-center organocatalysts, tartrate-derived diammonium salts (TaDiASs), are described. On the basis of conformational studies, optimized TaDiASs with a 2,6-disubstituted cyclohexane spiroacetal were newly designed. These TaDiASs catalyzed the asymmetric Michael and Mannich-type reactions of glycine Schiff bases with higher enantioselectivity than previous catalysts. In the Mannich-type reaction, aromatic N- Boc-protected imines (Boc = tert-butoxycarbonyl) as well as enolizable alkyl imines were applicable. As a synthetic application of the catalytic asymmetric Mannich-type reaction with the optimized TaDiASs. we developed a catalytic asymmetric total synthesis of (+)-nemonapride, which is an antipsychotic agent.

Original languageEnglish
Pages (from-to)794-801
Number of pages8
JournalChemistry - An Asian Journal
Volume2
Issue number6
DOIs
Publication statusPublished - Jun 25 2007
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Organic Chemistry

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