Lappaconitine-Catalyzed Asymmetric α-Hydroxylation of β-Keto Esters: A Bronsted Base Organocatalyst Developed from Terpenoid Alkaloids

被引：37

作者：

Gong, Bin ^{[1
]}

Meng, Qingwei ^{[1
]}

Su, Tian ^{[1
]}

Lian, Mingming ^{[1
]}

Wang, Qing ^{[1
]}

Gao, Zhanxian ^{[1
]}

机构：

[1] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116012, Peoples R China

来源：

SYNLETT | 2009年 / 16期

关键词：

lappaconitine; asymmetric alpha-hydroxylation; beta-keto esters; organocatalyst; terpenoid alkaloid; IMINIUM SALTS; ENANTIOSELECTIVE EPOXIDATION; CRYSTAL-STRUCTURE; ATOM-TRANSFER; OLEFINS; ALKENES; OXIDATION; ALDEHYDES;

D O I：

10.1055/s-0029-1217758

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Discovering organocatalysts with novel framework from terpenoid alkaloids is presented in this paper. Lappaconitine was found to enantioselectively catalyze alpha-hydroxylation of beta-keto esters using tert-butyl hydroperoxide as the oxidant in chloroform to afford the corresponding products in high yields and good enantioselectivity (up to 85% ee).

引用

页码：2659 / 2662

页数：4

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