A Divergent Approach to the Diastereoselective Synthesis of 3,3‐Disubstituted Oxindoles from Atropisomeric  N ‐Aryl Oxindole Derivatives | Zendy

Nakazaki Atsuo | Zendy; Mori Ayako | Zendy; Kobayashi Susumu | Zendy; Nishikawa Toshio | Zendy

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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.

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