C-O Versus C-C Bond Cleavage: Selectivity Control in Lewis Acid Catalyzed Chemodivergent Cycloadditions of Aryl Oxiranyldicarboxylates with Aldehydes, and Theoretical Rationalizations of Reaction Pathways

被引：58

作者：

Chen, Zuliang ^{[2
]}

Tian, Ziqi ^{[1
]}

Zhang, Jieming ^{[2
]}

Ma, Jing ^{[1
]}

Zhang, Junliang ^{[2
]}

机构：

[1] Nanjing Univ, Sch Chem & Chem Engn, Inst Theoret & Computat Chem, Key Lab Mesoscop Chem MOE, Nanjing 210093, Jiangsu, Peoples R China

[2] E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2012年 / 18卷 / 28期

关键词：

cleavage reactions; chemoselectivity; cycloaddition; Lewis acids; oxiranes; POLAR 3+2 CYCLOADDITION; ACTIVATED CARBONYL YLIDES; 1,3-DIPOLAR CYCLOADDITION; EPOXIDES; KETONES; 1,3-DIOXOLANES; OXIRANES; TANDEM;

D O I：

10.1002/chem.201201453

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A clean break: Lewis acid catalyzed chemodivergent [3+2] cycloadditions of aryl oxiranyldicarboxylates with aldehydes are revealed, in which the C-C or C-O bond cleavage of oxiranes can be controlled by the use of Ni(ClO 4) 2 or Sn(OTf) 2 catalysts (see scheme). Possible reaction pathways for these transformations are demonstrated by theoretical calculations. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：8591 / 8595

页数：5

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