Silyllithium-Initiated Coupling of alpha-Ketoamides with tert-Butanesulfinylimines for Stereoselective Synthesis of Enantioenriched alpha-(Silyloxy)-beta-amino Amides
Silyllithium-Initiated Coupling of alpha-Ketoamides with tert-Butanesulfinylimines for Stereoselective Synthesis of Enantioenriched alpha-(Silyloxy)-beta-amino Amides
复制标题
甲硅烷基锂引发的α-酮酰胺与叔丁烷亚磺酰亚胺的偶联用于立体选择性合成对映体富集的α-(甲硅烷氧基)-β-氨基酰胺
DOI：
10.1021/acs.orglett.6b00006
复制
发表时间：
2016
期刊：
影响因子：
5.2
通讯作者：
Xu Yan-Jun
中科院分区：
文献类型：
--
作者：
Sun Zhao;Liu Hui;Zeng Yong-Ming;Lu Chong-Dao;Xu Yan-Jun
A silyllithium-initiated coupling of α-ketoamides withtert-butanesulfinylimines was developed for the efficient, stereoselective synthesis of enantioenriched α-(silyloxy)-β-amino amides. Nucleophilic addition of silyllithium to α-ketoamides, followed by 1,2-Brook rearrangement, generates nucleophilic enolates, which are then intercepted by chiral imines to provide three-component coupling products. Use of α-ketoamides is critical for achieving high yields and diastereoselectivities in the resulting α-hydroxy-β-amino acid derivatives.
