Anti-selective glycolate aldol additions with an oxapyrone boron enolate

被引：69

作者：

Andrus, MB ^{[1
]}

Sekhar, BBVS ^{[1
]}

Meredith, EL ^{[1
]}

Dalley, NK ^{[1
]}

机构：

[1] Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 19期

关键词：

D O I：

10.1021/ol0002166

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

GRAPHICS The boron enolate of pyrone 2 undergoes asymmetric aldol reactions with aldehydes to give protected anti 1,2 diols 3. The pyrone is readily available from trans stilbene using asymmetric dihydroxylation. Yields for the aldol reaction range from 62 to 92% and the selectivities from 6:1 to >20:1 for the anti isomers, Protection and hydrogenolysis of the products can be used to remove the pyrone, giving differentially protected diol intermediates 12 that are amenable to multistep synthesis.

引用

页码：3035 / 3037

页数：3

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