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

Atsuo Nakazaki; Ayako Mori; Susumu Kobayashi; Toshio Nishikawa

doi:10.1002/asia.201601183

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

Chem Asian J. 2016 Nov 22;11(22):3267-3274. doi: 10.1002/asia.201601183. Epub 2016 Oct 18.

Authors

Atsuo Nakazaki¹, Ayako Mori¹, Susumu Kobayashi², Toshio Nishikawa¹

Affiliations

¹ Graduate School of Bioagricultural Sciences, Nagoya University, Furo-cho, Chikusa, Nagoya, 464-8601, Japan.
² Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba, 278-8510, Japan.

PMID: 27628126
DOI: 10.1002/asia.201601183

Abstract

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.

Keywords: 3,3-disubstituted oxindoles; C−N axial chirality; asymmetric synthesis; isatin.