Lewis Acid-Catalyzed Conjugate Additions of Silyloxyallenes: A Selective Solution to the Intermolecular Rauhut−Currier Problem

Silyloxyallenes serve as highly useful α-acylvinyl anion equivalents. These latent allenolates undergo conjugate additions to alkylidene malonates in the presence of 10 mol % Sc(OTf)3. The reaction delivers intermolecular Rauhut−Currier products in excellent yields and regioselectivities for a wide...

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Bibliographic Details
Published in:Organic letters 2008-06, Vol.10 (12), p.2449-2452
Main Authors: Reynolds, Troy E, Binkley, Michael S, Scheidt, Karl A
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Catalysis
Combinatorial Chemistry Techniques
Indicators and Reagents
Malonates - chemistry
Molecular Structure
Organosilicon Compounds - chemistry
Stereoisomerism
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Summary:Silyloxyallenes serve as highly useful α-acylvinyl anion equivalents. These latent allenolates undergo conjugate additions to alkylidene malonates in the presence of 10 mol % Sc(OTf)3. The reaction delivers intermolecular Rauhut−Currier products in excellent yields and regioselectivities for a wide scope of substrates. Notably, the formal cross-coupling of two different α,β-unsaturated carbonyl compounds (a cross Rauhut−Currier reaction) is achieved. Preliminary investigations have demonstrated good levels of enantioselectivity for the addition of a racemic silyloxyallene with a chiral Lewis acid.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol800745q