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Lewis Acid-Catalyzed Conjugate Additions of Silyloxyallenes: A Selective Solution to the Intermolecular Rauhut−Currier Problem
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Abstract
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.
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This article has been cited by 6 ACS Journal articles (5 most recent appear below).
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Development of a Cysteine-Catalyzed Enantioselective Rauhut−Currier Reaction
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Carrie E. Aroyan, Alpay Dermenci and Scott J. MillerThe Journal of Organic Chemistry2010 75 (17), 5784-5796Herein, we report a full account of the development of an enantioselective Rauhut−Currier process that affords products in high yields and enantioselectivities using a cysteine-based catalyst. While traditional Morita−Baylis−Hillman catalysts were found ...
Crossed Intramolecular Rauhut−Currier-Type Reactions via Dienamine Activation
Eugenia Marqués-López, Raquel P. Herrera, Timo Marks, Wiebke C. Jacobs, Daniel Könning, Renata M. de Figueiredo and Mathias ChristmannOrganic Letters2009 11 (18), 4116-4119Crossed Intramolecular Rauhut−Currier-Type Reactions via Dienamine Activation
Eugenia Marqués-López, Raquel P. Herrera, Timo Marks, Wiebke C. Jacobs, Daniel Könning, Renata M. de Figueiredo and Mathias ChristmannOrganic Letters2009 11 (18), 4116-4119The intramolecular Rauhut−Currier reaction creates a carbon−carbon bond between two tethered Michael acceptors. Previous asymmetric versions have relied on 1,4-additions of chiral nucleophilic catalysts. Herein, we investigate a novel strategy that ...
Acceleration of the Morita−Baylis−Hillman Reaction by a Simple Mixed Catalyst System
Alejandro Bugarin and Brian T. ConnellThe Journal of Organic Chemistry2009 74 (12), 4638-4641Acceleration of the Morita−Baylis−Hillman Reaction by a Simple Mixed Catalyst System
Alejandro Bugarin and Brian T. ConnellThe Journal of Organic Chemistry2009 74 (12), 4638-4641By using a catalytic amount of 4-dimethylaminopyridine (DMAP) as a nucleophile in the presence of an equal amount of tetramethylethylenediamine (TMEDA) and MgI2, Morita−Baylis−Hillman adducts can be obtained in good to excellent yields from various ...
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History
- Published In Issue June 19, 2008
- Article ASAPMay 14, 2008
- Received: April 02, 2008
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