Lewis Base Activation of Lewis Acids: Vinylogous Aldol Additions of Silyl Dienol Ethers to Aldehydes

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.

Lewis base - asymmetric catalysis - vinylogous aldol ­reactions - ketones - regioselectivity

References

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<A NAME="RY03604ST-10">10</A>

Catalyst (R,R)-1 is commercially available from Obiter Research, LLC, contact [e-mail].

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