A Divergent Approach to the Diastereoselective Synthesis of 3, 3‐Disubstituted Oxindoles from Atropisomeric N‐Aryl Oxindole Derivatives. Issue 22 (18th October 2016)

• Record Type: Journal Article
• Authors: Nakazaki, Atsuo; Mori, Ayako; Kobayashi, Susumu; Nishikawa, Toshio
• Is Part Of: Chemistry, an Asian journal. Volume 11:Issue 22(2016)
• Page Start: 3267
• Page End: 3274
• Publication Date: 2016-10-18
• Subjects: 3, 3-disubstituted oxindoles -- asymmetric synthesis -- C−N axial chirality -- isatin; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.201601183
• Languages: English
• ISSNs: 1861-4728

Abstract

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. 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.