Asymmetric Reaction of α-Diazomethylphosphonates with α-Ketoesters To Access Optically Active α-Diazo-β-hydroxyphosphonate Derivatives

被引：24

作者：

Du, Fei ^{[1
]}

Zhou, Jiao ^{[1
]}

Peng, Yungui ^{[1
]}

机构：

[1] Southwest Univ, Sch Chem & Chem Engn, Key Lab Appl Chem Chongqing Municipal, Chongqing 400715, Peoples R China

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 06期

基金：

美国国家科学基金会;

关键词：

ALDOL-TYPE REACTION; SEYFERTH-GILBERT REAGENT; CHIRAL DICARBOXYLIC-ACID; SACCHAROTHRIX SP ST-888; ETHYL DIAZOACETATE; DIAZOCARBONYL COMPOUNDS; MANNICH REACTION; ENANTIOSELECTIVE HYDROGENATION; FUNCTIONALIZED MOLECULES; CHEMOENZYMATIC SYNTHESIS;

D O I：

10.1021/acs.orglett.7b00128

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first example for asymmetric reaction of diazomethylphosphonates with alpha-ketoesters was realized in the catalysis of hydroquinidine-derived bifunctional thiourea. A methodology was established to access a series of chiral alpha-diazo-beta-hydroxyphosphonate derivatives containing various functional groups with high enantioselectivities and yields. The resulting products could be further transformed into chiral tertiary beta-hydroxyphosphonate and beta-halogenated fosfomycin derivatives, especially alpha-fluoride analogues.

引用

页码：1310 / 1313

页数：4

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