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

作者：Nakazaki Atsuo^*; Mori Ayako; Kobayashi Susumu; Nishikawa Toshio

来源：Chemistry-An Asian Journal, 2016, 11(22): 3267-3274.

DOI：10.1002/asia.201601183

• 3,3-disubstituted oxindoles
• asymmetric synthesis
• C-N axial chirality
• isatin

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.

• 出版日期2016-11-22