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One-pot, Three-Component Synthesis of Linearly Substituted Homoallylic Alcohols via Allyl(isopropoxy)dimethylsilane

Lianhai Li, Neenah Navasero

Org Lett. 2004 Sep 2;6(18):3091-4.

PMID: 15330595

Abstract:

[reaction: see text] A two-step approach that involves the synthesis of vinylsilane from allyl(isopropoxy)dimethylsilane (6) and the subsequent Pd-catalyzed cross-coupling of the resulting vinylsilane is applied in developing a novel diversity-oriented, three-component synthesis to homoallylic alcohols of common structure 1. Upon treatment of 6 with s-BuLi, the silylallylmetal 5 is generated and reacted with carbonyl compounds to produce functionalized vinylsilanes, which can couple with aryl/vinyl halides in the presence of palladium catalyst to afford 1.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP1825645 Isopropoxytrimethylsilane Isopropoxytrimethylsilane 1825-64-5 Price
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