Asymmetric Mannich reaction of imines derived from aliphatic and aromatic aldehydes catalyzed by diarylprolinol silyl ether

Tatsuya Urushima, Hayato Ishikawa, Yujiro Hayashi

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

Abstract

Anti Mannich, try this! A direct asymmetric Mannich reaction catalyzed by a diarylprolinol silyl ether was developed to afford the anti-Mannich product with excellent enantioselectivity. Imines derived from both aliphatic and aromatic aldehydes were successfully used to obtain the synthetically important β-amino aldehydes (see scheme; Ts=tosyl). The reaction can also be performed in the presence of water.

Original languageEnglish
Pages (from-to)8273-8276
Number of pages4
JournalChemistry - A European Journal
Volume17
Issue number30
DOIs
Publication statusPublished - 2011 Jul 18

Keywords

  • Mannich reaction
  • asymmetric synthesis
  • domino reactions
  • enantioselectivity
  • organocatalysis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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