Iterative stereospecific reagent-controlled homologation of pinacol boronates by enantioenriched α-chloroalkyllithium reagents

被引：109

作者：

Blakemore, Paul R. ^{[1
]}

Burge, Matthew S. ^{[1
]}

机构：

[1] Oregon State Univ, Dept Chem, Corvallis, OR 97331 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 11期

关键词：

D O I：

10.1021/ja068808s

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reaction of pinacol boronates with putative enantioenriched alpha-chloroalkyllithium species, generated in situ from homochiral alpha-chloroalkylsulfoxides by sulfoxide ligand exchange with t-BuLi in PhMe at -78 degrees C, gave chain-extended boronic ester products with generally excellent stereochemical fidelity. Iteration of this stereospecific reagent-controlled homologation (StReCH) process enabled the programmed synthesis of all four stereoisomers of a stereodiad-containing model system (4-benzyl-1,6-diphenylhexan-2-ol) with er >= 97:3 in all cases.

引用

页码：3068 / +

页数：3

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