Enantioselective Organocatalytic 1,6-Addition of Aziactones to &ITpara&IT-Quinone Methides: An Access to α,α-Disubstituted and β,β-Diaryl-α-amino acid Esters

被引：94

作者：

Li, Wenjun ^{[1
]}

Xu, Xianhong ^{[1
]}

Liu, Yang ^{[1
]}

Gao, Hua ^{[1
]}

Cheng, Yuyu ^{[2
]}

Li, Pengfei ^{[2
]}

机构：

[1] Qingdao Univ, Sch Pharm, Dept Med Chem, Qingdao 266021, Peoples R China

[2] Southern Univ Sci & Technol, Dept Chem, 1088 Xueyuan Blvd, Shenzhen 518055, Guangdong, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 04期

基金：

中国国家自然科学基金;

关键词：

ALPHA-AMINO-ACIDS; ASYMMETRIC 1,6-CONJUGATE ADDITION; BETA-SUBSTITUTED TRYPTOPHANS; MICHAEL ADDITION; ALPHA; BETA-UNSATURATED KETONES; DERIVATIVES; ALKYLATION; ALDEHYDES; PEPTIDES; ADDITION/AROMATIZATION;

D O I：

10.1021/acs.orglett.8b00072

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This work describes the first enantioselective 1,6-additions of azlactones to para-quinone methides. In the presence of a chiral phosphoric acid, 1,6-adducts were obtained in high yields (up to 96%) with excellent diastereoselectivities and enantioselectivities (all >20:1 dia-stereoselectivity ratio (dr), up to 99% enantiomeric excess (ee)). Importantly, the method offers a facile synthetic approach, not only to enantiopure alpha,alpha-disubstituted alpha-amino acid esters, but also to unnatural enantioenriched beta,beta-diaryl-alpha-amino acid esters bearing adjacent tertiary and quaternary stereogenic centers.

引用

页码：1142 / 1145

页数：4

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