Highly Enantioselective Conjugate Additions to α,β-Unsaturated Ketones Catalyzed by a (Salen)Al Complex

Chiral (salen)Al complex 1a catalyzes the highly enantioselective conjugate addition of carbon- and nitrogen-based nucleophiles to acyclic α,β-unsaturated ketones. This methodology is tolerant of substantial variation of the ketone structure, providing access to a wide range of useful chiral buildin...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2005-02, Vol.127 (4), p.1313-1317
Main Authors: Taylor, Mark S, Zalatan, David N, Lerchner, Andreas M, Jacobsen, Eric N
Format: Article
Language:English
Subjects:
Alkanes - chemistry
Aluminum - chemistry
Azides - chemistry
Catalysis
Chemistry
Ethylenediamines - chemistry
Exact sciences and technology
Ketones - chemistry
Nitriles - chemistry
Organic chemistry
Organometallic Compounds - chemistry
Stereoisomerism
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Summary:Chiral (salen)Al complex 1a catalyzes the highly enantioselective conjugate addition of carbon- and nitrogen-based nucleophiles to acyclic α,β-unsaturated ketones. This methodology is tolerant of substantial variation of the ketone structure, providing access to a wide range of useful chiral building blocks in high yield and enantiomeric excess. Synthetic manipulations of the conjugate addition products are demonstrated, including the straightforward preparation of β-amino ketones and highly enantioenriched carbo- and heterocyclic compounds.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja044999s