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

被引：66
|
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.
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收藏
页码：4990 / 4993
页数：4
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