Lewis Base Activation of Lewis Acids. Vinylogous Aldol Reactions
- 7 June 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 125 (26) , 7800-7801
- https://doi.org/10.1021/ja035448p
Abstract
A highly regioselective vinylogous aldol reaction catalyzed by SiCl4 and a chiral phosphoramide (R,R)-5, providing δ-hydroxy enones for a variety of aldehyde and dienol ether structures, has been developed. Low catalyst loadings (1 mol %) can be employed, giving the products in good yields, excellent enantioselectivities, and in some cases excellent anti diastereoselectivities. Both simple ester-derived dienol ethers as well as dioxanone-derived dienol ethers are employed. The observed regioselectivity is rationalized in terms of the sensitivity of the catalyst to the steric demands of the nucleophile.Keywords
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