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

Author(s): Hisahiro Hagiwara

Journal Name: Mini-Reviews in Organic Chemistry

Volume 1 , Issue 2 , 2004

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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

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Article Details

VOLUME: 1
ISSUE: 2
Year: 2004
Page: [169 - 182]
Pages: 14
DOI: 10.2174/1570193043488881
Price: $65

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