Mini-Reviews in Organic Chemistry

Author(s): Hisahiro Hagiwara

DOI: 10.2174/1570193043488881

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Highly Efficient and Environmentally Benign Catalytic Enamine Reaction of Unmodified Aldehydes and its Application to Terpenoid Syntheses

Page: [169 - 182] Pages: 14

  • * (Excluding Mailing and Handling)

Abstract

Unmodified aldehydes add in 1,4-manner to electron deficient olefins in the presence of a catalytic amount of diethylaminotrimethylsilane. Reaction with methyl α- haloacrylates provided formylcyclopropanecarboxylates by domino conjugate addition-alkylation. Aldol condensation afforded unsaturated aldehydes. The reaction was revealed to proceed via catalytic enamine pathway. Total syntheses of several bisabolane type sesquiterpenoids have been accomplished according to this protocol.

Keywords: diethylaminotrimethylsilane, conjugate addition, cyclopropanation, aldol condensation