Organobase-catalyzed [1,2]-Brook rearrangement of silyl glyoxylates

被引：64

作者：

Han, Man-Yi ^{[1
]}

Yang, Fei-Yan ^{[1
]}

Zhou, Di ^{[1
]}

Xu, Zhigang ^{[2
]}

机构：

[1] Huaibei Normal Univ, Dept Chem, Huaibei 235000, Anhui, Peoples R China

[2] Southwest Univ, Fac Mat & Energy, Chongqing Key Lab Adv Mat & Technol Clean Energie, Chongqing 400715, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 06期

基金：

中国国家自然科学基金;

关键词：

3-COMPONENT COUPLING REACTIONS; BROOK REARRANGEMENT; ORGANIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; LAMIVUDINE 3TC(TM); ACYLSILANES; CONSTRUCTION; DERIVATIVES; EFFICIENT; SILYLGLYOXYLATES;

D O I：

10.1039/c7ob00005g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient [1,2]-Brook rearrangement of silyl glyoxylates has been developed using DBU as the organobase-catalyst. This [1,2]-Brook rearrangement is applicable to a number of thiols and secondary phosphine oxides containing acidic protons. These nucleophiles afford the corresponding Brook products in high yields. Using this methodology, a formal synthesis of anti-HIV drug compound lamivudine was realized.

引用

页码：1418 / 1425

页数：8

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