Carbonyl-ene reaction: An emerging tool for acyclic stereocontrol.

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  • MIKAMI Koichi
    Department of Chemical Technology, Tokyo Institute of Technology
  • TERADA Masahiro
    Department of Chemical Technology, Tokyo Institute of Technology
  • SHIMIZU Masaki
    Department of Chemical Technology, Tokyo Institute of Technology
  • NAKAI Takeshi
    Department of Chemical Technology, Tokyo Institute of Technology

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Other Title
  • カルボニル‐エン反応：新しい鎖状立体制御法
  • カルボニル エン ハンノウ アタラシイ サジョウ リッタイ セイギョホウ

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Description

The ene reaction involving 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.<BR>The carbonyl-ene reactions are shown to provide high levels of diastereocontrol, diastereofacial control, olefinic stereocontrol, and/or 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.

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