Highly Enantiospecific Borylation for Chiral α-Amino Tertiary Boronic Esters

被引：19

作者：

Qi, Qingqing ^{[1
]}

Yang, Xuena ^{[1
]}

Fu, Xiaoping ^{[1
]}

Xu, Shiqing ^{[1
]}

Negishi, Ei-ichi ^{[1
]}

机构：

[1] Purdue Univ, Herbert C Brown Labs Chem, 560 Oval Dr, W Lafayette, IN 47907 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 46期

关键词：

alpha-aminoboronates; asymmetric synthesis; borylation; quaternary centers; rotamer; CROSS-COUPLING REACTIONS; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; LITHIATION-SUBSTITUTION; STEREOSELECTIVE-SYNTHESIS; PINACOLBORYL ADDITION; ACID-DERIVATIVES; HYDROBORATION; ARYL; SECONDARY;

D O I：

10.1002/anie.201809389

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein we report a highly efficient and enantiospecific borylation method to synthesize a wide range of enantiopure (>99% ee) alpha-amino tertiary boronic esters. The configurationally stable alpha-N-Boc substituted tertiary organo-lithium species and pinacolborane (HBpin) underwent enantiospecific borylation at 78 degrees C with the formation of a new stereogenic C-B bond. This reaction has a broad scope, enabling the synthesis of various a-amino tertiary boronic esters in excellent yields and, importantly, with universally excellent enantiospecificity (>99% es) and complete retention of configuration.

引用

页码：15138 / 15142

页数：5

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