Asymmetric Synthesis of 3,3-Disubstituted Oxindoles from N-Aryl Oxindole Derivatives bearing C-N Axial Chirality

被引：1

作者：

Nakazaki, Atsuo ^{[1
]}

机构：

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

来源：

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN | 2017年 / 75卷 / 08期

关键词：

3,3-disubstituted oxindole; asymmetric synthesis; N-aryl isatin; C-N axial chirality; ortho-azaxylylene; N-arylation; divergent synthesis; CATALYTIC ENANTIOSELECTIVE SYNTHESIS; CONCISE TOTAL-SYNTHESIS; CLAISEN REARRANGEMENT; ENOLATE CHEMISTRY; DIASTEREOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; EFFICIENT SYNTHESIS; ALKALOIDS; SPIROOXINDOLES; ARYLATION;

D O I：

10.5059/yukigoseikyokaishi.75.821

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have newly designed N-aryl oxindole with C-N axial chirality as a common intermediate for diastereoselective and divergent synthesis of a variety of 3,3-disubstituted oxindoles bearing a C3 stereogenic center. High diastereoselectivities (up to >95:<5) were observed with orthomonosubstituted N-aryl oxindole systems through transformations including nucleophilic addition, alkylation, and cycloaddition. Facile removal of the p-(benzyloxy) aryl moiety in axially twisted amides was achieved by a mild, two-step sequence. We also describe the first synthesis of an enantiomerically pure C-N axially chiral N-aryl isatin from the corresponding N-aryl oxindole, which was synthesized by an asymmetric intramolecular Buchwald-Hartwig N-arylation.

引用

页码：821 / 830

页数：10

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