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Synlett 2009(10): 1525-1542
DOI: 10.1055/s-0029-1217350
DOI: 10.1055/s-0029-1217350
ACCOUNT
© Georg Thieme Verlag
Stuttgart ˙ New York
Advances in Exploring Heterocyclic Dienoxysilane Nucleophiles in Asymmetric Synthesis
Further Information
Received
4 December 2008
Publication Date:
02 June 2009 (online)
Publication History
Publication Date:
02 June 2009 (online)
Abstract
The synthetic versatility of a special collection of heterocyclic dienoxysilane synthons based on furan, pyrrole, and thiophene to access valuable building blocks to be used in the fabrication of complex molecular architectures is featured. Accessed by base-assisted enolsilylation of α,β-unsaturated lactone or lactam precursors, siloxydiene heterocycles easily couple in a strictly vinylogous sense to diverse electrophiles, such as aldol-, Mannich-, and Michael-type acceptors, to generate butenolide-type intermediates for viable use in asymmetric synthesis. A survey of our own achievements in this area, along with preeminent contributions by other research groups reveal the unique merits of siloxydiene chemistry and highlight these reactions as a key gateway to an array of multifunctional natural or natural-like constructs.
1 Introduction
2 Synthetic Applications
2.1 Vinylogous Mukaiyama Aldol-type Additions
2.2 Vinylogous Mukaiyama Mannich-type Additions
2.3 Vinylogous Mukaiyama Michael-type Additions
3 Prospects, Challenges, and Opportunities
4 Addendum
Key words
siloxydiene heterocycles - vinylogous Mukaiyama aldol additions - vinylogous Mukaiyama Mannich additions - vinylogous Mukaiyama Michael additions - asymmetric synthesis
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