Stereoselective Arylation of Amino Aldehydes: Overriding Natural Substrate Control through Chelation

被引：5

作者：

Martins, Bruna S. ^{[1
]}

Moro, Angelica V. ^{[1
]}

Luedtke, Diogo S. ^{[1
]}

机构：

[1] Univ Fed Rio Grande, Inst Quim, UFRGS, Av Bento Gonsalves 9500, BR-91501970 Porto Alegre, RS, Brazil

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 06期

关键词：

PRACTICAL CHIRAL AUXILIARY; CONTROLLED ADDITIONS; DIASTEREOSELECTIVE ARYLATION; ASYMMETRIC-SYNTHESIS; ZINC EXCHANGE; ACIDS; ALCOHOLS; BORON; PSEUDOEPHENAMINE; PSEUDOEPHEDRINE;

D O I：

10.1021/acs.joc.7b00215

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chelation-controlled arylation reaction of chiral, enantiopure acyclic alpha-amino aldehydes enabled by a B/Zn exchange reaction between arylboronic acids and Et2Zn is reported. The presence of dibenzyl substituents at the nitrogen plays a key role in the stereochemical outcome of the reaction, and chelation is favored over the natural tendency of this type of substrate to undergo Felkin-Anh controlled additions with organomagnesium and organolithium reagents.

引用

页码：3334 / 3340

页数：7

共 43 条

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