Premium
Synthesis of Enantiomerically Pure (α‐Phenylalkyl)amines with Substituents at the ortho Position through Diastereoselective Radical Alkylation Reaction of Sulfinimines
Author(s) -
FernándezSalas José A.,
RodríguezFernández M. Mercedes,
Maestro M. Carmen,
GarcíaRuano José L.
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402355
Subject(s) - chemistry , isopropyl , alkylation , alkyl , chiral auxiliary , medicinal chemistry , regioselectivity , stereochemistry , enantioselective synthesis , organic chemistry , catalysis
The alkyl radical (R 1 ) addition reaction to ortho ‐X‐substituted N ‐(benzylidene)‐2‐methylpropane‐2‐sulfinamides (X = Br, CN, CO 2 Me, 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 α‐( tert ‐butyl)‐ ortho ‐hydroxy‐ and ‐ ortho ‐methoxybenzylamines, as well as the 3‐isopropyl‐substituted isoindolin‐1‐one.