Diastereoselective Synthesis of 3,3-Disubstituted Oxindoles from N-Aryl-3-Chlorooxindoles Bearing C-N Axial Chirality via Nucleophilic Substitution

作者：Nakazaki Atsuo^*; Miyagawa Keitaro; Nishikawa Toshio

来源：Synlett, 2015, 26(8): 1116-1120.

DOI：10.1055/s-0034-1380266

• 3
• 3-disubstituted oxindole
• C-N axial chirality
• ortho-azaxylylene

Diastereoselective synthesis of 3,3-disubstituted oxindoles was examined using racemic N-aryl-3-chlorooxindoles bearing C-N axial chirality. The reaction involved the nucleophilic substitution of 3-chlorooxindoles via an ortho-azaxylylene intermediate in the presence of AgBF4 and MS 4 angstrom. High diastereoselectivities (up to >95:<5) were achieved in the formation of 3-alkyl-3-aryloxindole derivatives when electron-rich arenes were used.

• 出版日期2015-5