Functionalization of α,β-unsaturated esters and ketones:: A facile and highly stereoselective one-pot approach to N-protected α,β-dehydroamino acid derivatives

被引：66

作者：

Chen, DJ

Guo, L

Liu, JY

Kirtane, S

Cannon, JF

Li, GG ^{[1
]}

机构：

[1] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA

[2] Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 05期

关键词：

D O I：

10.1021/ol050002u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new, facile, and highly stereoselective protocol toward alpha,beta-dehydroamino acid derivatives has been developed. The one-pot synthesis was very convenient to perform by using the aminohalogenation reaction of alpha,beta-unsaturated esters and ketones followed by treatment with specific bases. Only two [2.2.2] bicyclic organic bases were found to be effective for this transformation. Good yields (58-68%) and excellent Z-selectivity were obtained for 12 examples.

引用

页码：921 / 924

页数：4

共 50 条

[1]

BAHC T, 2000, CHEM COMMUN, P287

[2] REACTIONS OF RELEVANCE TO CHEMISTRY OF AMINOGLYCOSIDE ANTIBIOTICS .9. NEW REAGENTS FOR AMINATION OF ETHYLENIC LINKAGE [J].