Synthesis of Enantiomerically Pure (α-Phenylalkyl)amines with Substituents at the ortho Position through Diastereoselective Radical Alkylation Reaction of Sulfinimines

被引：18
作者：
Fernandez-Salas, Jose A. [1 ]
Mercedes Rodriguez-Fernandez, M. [1 ]
Carmen Maestro, M. [1 ]
Garcia-Ruano, Jose L. [1 ]
机构：
[1] Univ Autonoma Madrid, Dept Organ Chem, E-28049 Madrid, Spain
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 24期
关键词：
Synthetic methods; Chiral auxiliaries; Radical reactions; Sulfinimines; Diastereoselectivity; CONCISE ASYMMETRIC-SYNTHESIS; TERT-BUTANESULFINYL IMINES; CARBONYL-COMPOUNDS; CHIRAL HYDRAZONES; CATALYSTS; AMINES; EFFICIENT; FUNCTIONALIZATION; ISOINDOLINONES; ALDIMINES;
D O I：
10.1002/ejoc.201402355
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The alkyl radical (R-1) addition reaction to ortho-X-substituted N-(benzylidene)-2-methylpropane-2-sulfinamides (X = Br, CN, CO2Me, OH and OMe) is highly diastereoselective, regardless of the electronic properties of the X group and the size of R-1. Easy removal of the sulfinyl group provides the title compounds in enantiomerically pure form. This two-step sequence has been successfully applied to the preparation of primary alpha-(tert-butyl)-ortho-hydroxy- and -ortho-methoxy-benzylamines, as well as the 3-isopropyl-substituted isoindolin-1-one.
引用
收藏
页码：5265 / 5272
页数：8
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