Asymmetric Substitution at the Tetrasubstituted Chiral Carbon: Catalytic Ring-Opening Alkylation of Racemic 2,2-Disubstituted Aziridines with 3-Substituted Oxindoles

被引：108

作者：

Ohmatsu, Kohsuke ^{[1
,2
]}

Ando, Yuichiro ^{[1
,2
]}

Ooi, Takashi ^{[1
,2
,3
]}

机构：

[1] Nagoya Univ, Grad Sch Engn, Inst Transformat Biomol WPI ITbM, Nagoya, Aichi 4648603, Japan

[2] Nagoya Univ, Grad Sch Engn, Dept Appl Chem, Nagoya, Aichi 4648603, Japan

[3] Japan Sci & Technol Agcy JST, CREST, Nagoya, Aichi 4648603, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 50期

关键词：

TERTIARY BORONIC ESTERS; QUATERNARY CARBON; ENANTIOSELECTIVE CONSTRUCTION; STEREOSPECIFIC CONSTRUCTION; PROMOTED REARRANGEMENT; SECONDARY ALCOHOLS; ALLYLIC ALKYLATION; KINETIC RESOLUTION; MESO-AZIRIDINES; ALPHA-HYDROXY;

D O I：

10.1021/ja411647x

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly diastereo- and enantioselective ring-opening alkylation of racemic 2,2-disubstituted aziridines with 3-substituted oxindoles is achieved under the catalysis of a chiral 1,2,3-triazolium salt. This reaction represents a hitherto unknown, catalytic stereoselective carbon carbon bond formation through direct substitution at the tetrasubstituted chiral carbon.

引用

页码：18706 / 18709

页数：4

共 65 条

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