Enantioselective Syntheses of (+)-Sertraline and (+)-Indatraline Using Lithiation/Borylation-Protodeboronation Methodology

被引：82

作者：

Roesner, Stefan ^{[1
]}

Casatejada, Javier Mansilla ^{[1
]}

Elford, Tim G. ^{[1
]}

Sonawane, Ravindra P. ^{[1
]}

Aggarwal, Varinder K. ^{[1
]}

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 21期

基金：

英国工程与自然科学研究理事会; 欧洲研究理事会;

关键词：

TERTIARY BORONIC ESTERS; ASYMMETRIC-SYNTHESIS; ELECTROPHILIC SUBSTITUTION; SECONDARY ALCOHOLS; SERTRALINE; DIASTEREOSELECTIVITY; GENERATION; CONVERSION; REDUCTION; SEROTONIN;

D O I：

10.1021/ol202251p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The lithiation/borylation-protodeboronation of a homoallyl carbamate was applied to the synthesis of (+)-sertraline and (+)-indatraline. Due to the presence of the alkene, significant modifications of the methodology were required (use of 12-crown-4, TMSCI, H2O), or a solvent switch to CHCI3, to achieve high yields and high selectivities.

引用

页码：5740 / 5743

页数：4

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