The direct, enantioselective, one-pot, three-component, cross-Mannich reaction of aldehydes: The reason for the higher reactivity of aldimine versus aldehyde in proline-mediated Mannich and aldol reactions

Yujiro Hayashi, Tatsuya Urushima, Mitsuru Shoji, Tadafumi Uchimaru, Isamu Shiina

Research output: Contribution to journalArticle

43 Citations (Scopus)

Abstract

In the proline-mediated Mannich and aldol reactions of propanal as a nucleophile, the aldimine prepared from benzaldehyde and p-anisidine is about 7 times more reactive than the corresponding aldehyde, benzaldehyde, as an electrophile. This higher reactivity of aldimine over aldehyde is attributed to the carboxylic acid of proline protonating the basic nitrogen atom of the aldimine more effectively than the oxygen atom of the aldehyde, an explanation which has been both experimentally and theoretically verified.

Original languageEnglish
Pages (from-to)1595-1604
Number of pages10
JournalAdvanced Synthesis and Catalysis
Volume347
Issue number11-13
DOIs
Publication statusPublished - 2005 Oct

Keywords

  • Asymmetric synthesis
  • Imines
  • Mannich reaction
  • Organocatalysis
  • Proline

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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