Enantioselective Cyclopropanation of Indoles: Construction of All-Carbon Quaternary Stereocenters

被引：67

作者：

Oezueduru, Guelsuem ^{[1
]}

Schubach, Thea ^{[1
]}

Boysen, Mike M. K. ^{[1
]}

机构：

[1] Leibniz Univ Hannover, Inst Organ Chem, D-30167 Hannover, Germany

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 19期

关键词：

CATALYTIC ASYMMETRIC-SYNTHESIS; FORMAL TOTAL-SYNTHESIS; ORGANIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; BIS(OXAZOLINE) LIGANDS; RING-SYSTEM; PHYSOSTIGMINE; ALKALOIDS; CENTERS; COMPLEX;

D O I：

10.1021/ol302388t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first enantioselective copper-catalyzed cyclopropanation of N-acyl indoles is described. Using carbohydrate-based bis(oxazoline) ligands (glucoBox), the products were obtained in up to 72% ee. Cyclopropanation of N-Boc 3-methyl indole yielded a product with an all-carbon quaternary stereocenter, which is a valuable building block for the synthesis of indole alkaloids: Deprotection and rearrangement gave a tricyclic hemiaminal ester in 96% ee, which was subsequently employed as a key intermediate for the synthesis of (-)-desoxyeseroline.

引用

页码：4990 / 4993

页数：4

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