Organocatalytic 1,4-Addition Reaction of α,β-γ,δ-Diunsaturated Aldehydes versus 1,6-Addition Reaction

Yujiro Hayashi, Daichi Okamura, Shigenobu Umemiya, Tadafumi Uchimaru

Research output: Contribution to journalArticlepeer-review

43 Citations (Scopus)

Abstract

Among 1,4-addition and 1,6-addition reactions, 1,4-addition reaction is the main reaction mode in the Michael reaction of α,β-γ,δ-diunsaturated aldehyde with several nucleophiles catalyzed by diphenylprolinol silyl ether via iminium ion intermediate. The 1,4-addition products, which possess excellent enantioselectivity and alkene moiety, are useful chiral building blocks. The abinitio calculation indicates that 1,4-addition reaction is preferable in terms of π-orbital coefficient and Mulliken/CHelpG atomic charge.

Original languageEnglish
Pages (from-to)959-962
Number of pages4
JournalChemCatChem
Volume4
Issue number7
DOIs
Publication statusPublished - 2012 Jul 1
Externally publishedYes

Keywords

  • Asymmetric reaction
  • Calculation
  • Michael reaction
  • Organocatalysis

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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