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A Divergent Approach to the Diastereoselective Synthesis of 3,3‐Disubstituted Oxindoles from Atropisomeric N ‐Aryl Oxindole Derivatives
Author(s) -
Nakazaki Atsuo,
Mori Ayako,
Kobayashi Susumu,
Nishikawa Toshio
Publication year - 2016
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201601183
Subject(s) - oxindole , moiety , aryl , chemistry , cycloaddition , sequence (biology) , alkylation , atropisomer , nucleophile , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , alkyl , biochemistry
3,3‐Disubstituted oxindoles were divergently synthesized by diastereoselective transformations including nucleophilic addition, alkylation, and cycloaddition using common, axially chiral N ‐aryl oxindoles. Notably, high diastereoselectivities (up to >95:5) were observed with ortho ‐monosubstituted N ‐aryl oxindoles to give various oxindole scaffolds, and facile removal of the p ‐(benzyloxy)aryl moiety in axially twisted amides was achieved by a mild, two‐step sequence.