Carbonyl-Ene Reaction: An Emerging Tool for Acyclic Stereocontrol

Koichi Mikam, Masahiro Terada, Masaki Shimizu, Takeshi Nakai

Research output: Contribution to journalArticlepeer-review

37 Citations (Scopus)

Abstract

The ene reaction involing a carbonyl compound, an aldehyde in particular, as an enophile should, in principle, constitute a more efficient alternative to the carbonyl addition reaction of allylmetals which has now become one of the most useful methods for acyclic stereocontrol. We describe herein the new efficient methods for acyclic stereocontrol based on the carbonyl-ene reaction promoted or catalyzed by the Lewis acid. The carbonyl-ene reactions are shown to provide high levels of diastereocontrol, diastereofacial control, ole-finic stereocontrol, andJor catalyst-based enantiofacial control, depending heavily on the characteristic feature of the achiral or chiral Lewis acid employed. Thus, the carbonyl-ene methodology is more advantageous than the allylmetal methodology for acyclic stereocontrol in terms of the easy availability of the olefin (ene) and the operational simplicity, along with the high levels of stereoselection.

Original languageEnglish
Pages (from-to)292-303
Number of pages12
JournalJournal of Synthetic Organic Chemistry, Japan
Volume48
Issue number4
DOIs
Publication statusPublished - 1990 Jan 1
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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