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

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

Volume: 1 Issue: 2

Author(s): Hisahiro Hagiwara

Affiliation:

Keywords: diethylaminotrimethylsilane, conjugate addition, cyclopropanation, aldol condensation

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.

Cite this article as:

Hagiwara Hisahiro, Highly Efficient and Environmentally Benign Catalytic Enamine Reaction of Unmodified Aldehydes and its Application to Terpenoid Syntheses, Mini-Reviews in Organic Chemistry 2004; 1 (2) . https://dx.doi.org/10.2174/1570193043488881