4.7 Article

Highly enantioselective synthesis of (E)-Allylic Alcohols

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JOURNAL OF ORGANIC CHEMISTRY
卷 72, 期 15, 页码 5935-5937

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AMER CHEMICAL SOC
DOI: 10.1021/jo0709403

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The asymmetric addition of alkenylzincs to aromatic and alpha-branched aliphatic aldehydes catalyzed by 1 generated the corresponding (E)-allylic alcohols with > 95% ee and good to excellent chemical yields, especially > 99.5% ee was observed in the case of 4-CF3-benzaldehyde. Notably, 1 is an effective ligand to catalyze the addition of disubstituted (R-2 = R-3 = ethyl) and bulky substituted (R-2 = H, R-3 = tert-butyl) alkenylzincs to benzaldehyde, affording the corresponding allylic alcohols both with 96% ee.

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