Site-selective benzoin-type cyclization of unsymmetrical dialdoses catalyzed by N-heterocyclic carbenes for divergent cyclitol synthesis

被引：14

作者：

Kang, Bubwoong ^{[1
]}

Wang, Yinli ^{[1
]}

Kuwano, Satoru ^{[1
]}

Yamaoka, Yousuke ^{[1
]}

Takasu, Kiyosei ^{[1
]}

Yamada, Ken-ichi ^{[1
,2
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

[2] Univ Tokushima, Grad Sch Pharmaceut Sci, Tokushima 7708505, Japan

来源：

CHEMICAL COMMUNICATIONS | 2017年 / 53卷 / 32期

关键词：

CHIRAL BUILDING-BLOCK; ACYLOIN CONDENSATION; KINETIC RESOLUTION; SECONDARY ALCOHOLS; THIAZOLIUM SALT; LEAVING GROUP; ALDEHYDES; INOSITOLS; QUEBRACHITOL; CONDURITOLS;

D O I：

10.1039/c7cc01191a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly site-selective N-heterocyclic carbene (NHC)-catalyzed benzoin-type cyclization of unsymmetrical dialdoses is developed to enable a divergent cyclitol synthesis. The choice of chiral NHCs and protecting groups affects the site-selectivity. The resulting inososes are converted into epi- ,muco- and myo-inositols, and their chiral protected derivatives are formed in good yields.

引用

页码：4469 / 4472

页数：4

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