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Synlett 2004(13): 2411-2416
DOI: 10.1055/s-2004-834789
DOI: 10.1055/s-2004-834789
CLUSTER
© Georg Thieme Verlag Stuttgart · New York
Lewis Base Activation of Lewis Acids: Vinylogous Aldol Additions of Silyl Dienol Ethers to Aldehydes
Further Information
Received
1 July 2004
Publication Date:
07 October 2004 (online)
Publication History
Publication Date:
07 October 2004 (online)
Abstract
Highly regioselective vinylogous aldol additions of silyl dienol ethers derived from simple α,β-unsaturated ketones are described. The catalyst system of silicon tetrachloride activated by chiral bisphosphoramide (R,R)-1 effectively promotes the addition of both γ-substituted and unsubstituted silyl dienol ethers to a variety of aldehydes with exclusive γ-regioselectivity and good to excellent diastereo- and enantioselectivity.
Key words
Lewis base - asymmetric catalysis - vinylogous aldol reactions - ketones - regioselectivity
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References
Catalyst (R,R)-1 is commercially available from Obiter Research, LLC, contact waboulanger@obiterresearch.com.