Asymmetric Catalytic 1,3-Dipolar Cycloaddition Reaction of Nitrile Imines for the Synthesis of Chiral Spiro-Pyrazoline-Oxindoles

被引：119

作者：

Wang, Gang ^{[1
]}

Liu, Xiaohua ^{[1
]}

Huang, Tianyu ^{[1
]}

Kuang, Yulong ^{[1
]}

Lin, Lili ^{[1
]}

Feng, Xiaoming ^{[1
]}

机构：

[1] Sichuan Univ, Minist Educ, Coll Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 01期

基金：

中国国家自然科学基金;

关键词：

HIGHLY ENANTIOSELECTIVE SYNTHESIS; AZOMETHINE IMINES; NITRONES; YLIDES; CONSTRUCTION; DIAZOESTERS; ISATINS; KETONES;

D O I：

10.1021/ol303097j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new 1,3-dipolar cycloaddition of nitrile imines with 3-alkenyl-oxindoles was catalyzed by a new chiral Mg(ClO4)(2) complex of an N,N'-dioxide ligand. The reaction is so far the sole catalytic synthesis of spiro-pyrazoline-oxindole derivatives. A wide variety of substrates were explored to obtain good yields (up to 98%) and excellent enantioselectivities (up to 99%). This cycloaddition expands the scope of propargyl anion type 1,3-dipole in the construction of 2-pyrazoline subunit.

引用

页码：76 / 79

页数：4

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