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

被引：5

作者：

Nakazaki, Atsuo ^{[1
]}

Miyagawa, Keitaro ^{[1
]}

Nishikawa, Toshio ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Bioagr Sci, Chikusa Ku, Nagoya, Aichi 4648601, Japan

来源：

SYNLETT | 2015年 / 26卷 / 08期

关键词：

3; 3-disubstituted oxindole; C-N axial chirality; ortho-azaxylylene; CATALYTIC ASYMMETRIC-SYNTHESIS; CONCISE TOTAL-SYNTHESIS; CLAISEN REARRANGEMENT; ENANTIOSELECTIVE SYNTHESIS; NATURAL-PRODUCTS; STEREOSELECTIVE-SYNTHESIS; EFFICIENT SYNTHESIS; ALKALOIDS; SPIROOXINDOLES; CONSTRUCTION;

D O I：

10.1055/s-0034-1380266

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：1116 / 1120

页数：5

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