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- W2157082813 abstract "The generality of Lewis base catalyzed, Lewis acid mediated, enantioselective vinylogous aldol addition reactions has been investigated. The combination of silicon tetrachloride and chiral phosphoramides is a competent catalyst for highly selective additions of a variety of α,β-unsaturated ketone-, 1,3-diketone-, and α,β-unsaturated amide-derived dienolates to aldehydes. These reactions provided high levels of γ-site selectivity for a variety of substitution patterns on the dienyl unit. Both ketone- and morpholine amide-derived dienol ethers afforded high enantio- and diastereoselectivity in the addition to conjugated aldehydes. Although α,β-unsaturated ketone-derived dienolate did not react with aliphatic aldehydes, α,β-unsaturated amide-derived dienolates underwent addition at reasonable rates affording high yields of vinylogous aldol product. The enantioselectivities achieved with the morpholine derived-dienolate in the addition to aliphatic aldehydes was the highest afforded to date with the silicon tetrachloride−chiral phosphoramide system. Furthermore, the ability to cleanly convert the morpholine amide to a methyl ketone was demonstrated." @default.
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- W2157082813 date "2007-06-21" @default.
- W2157082813 modified "2023-09-30" @default.
- W2157082813 title "Lewis Base Activation of Lewis Acids: Catalytic, Enantioselective Vinylogous Aldol Addition Reactions" @default.
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- W2157082813 doi "https://doi.org/10.1021/jo070638u" @default.
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