Asymmetric 1,3-dipolar cycloadditions of acrylamides

被引：252

作者：

Kissane, Marie ^{[1
]}

Maguire, Anita R. ^{[1
,2
]}

机构：

[1] Natl Univ Ireland Univ Coll Cork, Dept Chem, Analyt & Biol Chem Res Facil, Cork, Ireland

[2] Natl Univ Ireland Univ Coll Cork, Analyt & Biol Chem Res Facil, Sch Pharm, Cork, Ireland

来源：

CHEMICAL SOCIETY REVIEWS | 2010年 / 39卷 / 02期

关键词：

NITRILE OXIDE CYCLOADDITIONS; CHIRAL AZOMETHINE YLIDES; ENANTIOSELECTIVE TOTAL-SYNTHESIS; CONVERGENT FUNCTIONAL-GROUPS; X=Y-ZH COMPOUNDS; DIELS-ALDER; CATALYZED 1,3-DIPOLAR; DIPOLAR CYCLOADDITION; STEREOSELECTIVE-SYNTHESIS; NITRONE CYCLOADDITIONS;

D O I：

10.1039/b909358n

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This critical review, which is relevant to researchers in synthetic organic chemistry, focuses on asymmetric 1,3-dipolar cycloadditions with acrylamides. The use of chiral acrylamides as dipolarophiles leads to high levels of stereocontrol, due to conformational constraint in the acrylamides. Employment of chiral tertiary acrylamides containing nitrogen heterocycles is particularly effective in controlling the stereoselectivity. Following a general overview of 1,3-dipolar cycloadditions, the main body of the review focuses on asymmetric 1,3-dipolar cycloadditions of acrylamides with nitrile oxides, nitrones, diazoalkanes and azomethine ylides, with particular emphasis on the rationale for the observed stereocontrol (215 references).

引用

页码：845 / 883

页数：39

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