Controlling Asymmetric Remote and Cascade 1,3-Dipolar Cycloaddition Reactions by Organocatalysis

被引：48

作者：

Poulsen, Pernille H. ^{[1
]}

Vergura, Stefania ^{[1
]}

Monleon, Alicia ^{[1
]}

Jorgensen, Danny Kaare Bech ^{[1
]}

Jorgensen, Karl Anker ^{[1
]}

机构：

[1] Aarhus Univ, Dept Chem, Langelandsgade 140, DK-8000 Aarhus C, Denmark

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2016年 / 138卷 / 20期

关键词：

ALPHA; BETA-UNSATURATED ALDEHYDES; ONE-POT; ORGANIC-SYNTHESIS; HIGHLY REGIO; NITRONES; 2,4-DIENALS; ISOXAZOLIDINES; STEREOCENTERS; AZIRIDINATION; DERIVATIVES;

D O I：

10.1021/jacs.6b03546

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The regio- and stereoselective control of cycloaddition reactions to polyconjugated systems has been demonstrated by applying asymmetric organo-catalysis. Reaction of 2,4-dienals with nitrones allows for a highly regio- and stereoselective 1,3-dipolar cycloaddition in the presence of an aminocatalyst. The first cycloaddition on the remote olefin can be followed either by a cascade reaction or by other selective reactions of the remaining olefin. The chiral products are obtained in good to high yields and excellent diastereo- and enantioselectivities. The remote selective concept has been extended to 2,4,6-trienals by means of a novel enantioselective triple cascade 1,3-dipolar cycloaddition reaction. The formation of chiral poly 1,3-amino alcohols is also demonstrated.

引用

页码：6412 / 6415

页数：4

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