Direct organocatalytic Mannich reaction of acetaldehyde: An improved catalyst and mechanistic insight from a computational study

Yujiro Hayashi, Tsubasa Okano, Takahiko Itoh, Tatsuya Urushima, Hayato Ishikawa, Tadafumi Uchimaru

Research output: Contribution to journalArticle

98 Citations (Scopus)

Abstract

(Chemical Equation Presented) A chiral diaryl prolinol silyl ether organocatalyst with an acidis used for the direct catalytic asymmetric Mannich reaction of acetaldehyde and imines. N-Benzoyl-, N-tert-butoxycarbonyl-, and N-toluene-4-sulfonylimines can be employed to produce synthetically useful β-amino aldehydes in goodyield s andwith excellent enantioselectivity (see scheme). The reaction mechanism was investigated quantum-mechanically.

Original languageEnglish
Pages (from-to)9053-9058
Number of pages6
JournalAngewandte Chemie - International Edition
Volume47
Issue number47
DOIs
Publication statusPublished - 2008 Nov 10
Externally publishedYes

Keywords

  • Acetaldehyde
  • Asymmetric catalysis
  • Imines
  • Mannich reactions
  • Organocatalysis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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