Highly Enantioselective One-Pot Synthesis of Chiral β-Hydroxy Sulfones via Asymmetric Transfer Hydrogenation in an Aqueous Medium

被引：36

作者：

Zhang, Dacheng ^{[1
]}

Cheng, Tanyu ^{[1
]}

Zhao, Qiankun ^{[1
]}

Xu, Jianyou ^{[1
]}

Liu, Guohua ^{[1
]}

机构：

[1] Shanghai Normal Univ, Key Lab Resource Chem, Shanghai Key Lab Rare Earth Funct Mat, Minist Educ, Shanghai 200234, Peoples R China

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 21期

关键词：

BAKERS-YEAST REDUCTION; KETO-SULFONES; CASCADE REACTIONS; EFFICIENT SYNTHESIS; AROMATIC KETONES; CATALYSIS; LIGANDS; WATER; BUTENOLIDES; RESOLUTION;

D O I：

10.1021/ol502832a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild transformation in an aqueous medium for the one-pot synthesis of optically active beta-hydroxy sulfones is described. The intermediates of beta-keto sulfones obtained via a nucleophilic substitution reaction of alpha-bromoketones and sodium sulfinates in H2O/MeOH (1:3, v/v) at 50 degrees C were reduced through Ru-catalyzed asymmetric transfer hydrogenation in one-pot using HCOONa as a hydrogen source providing a variety of chiral beta-hydroxy sulfones with high yields and excellent enantioselectivities.

引用

页码：5764 / 5767

页数：4

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