On the Role of DNA in DNA-based Catalytic Enantioselective Conjugate Addition Reactions

被引：26

作者：

Dijk, Ewold W. ^{[1
]}

Boersma, Arnold J. ^{[1
]}

Feringa, Ben L. ^{[1
]}

Roelfes, Gerard ^{[1
]}

机构：

[1] Univ Groningen, Stratingh Inst Chem, NL-9747 AG Groningen, Netherlands

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 17期

关键词：

DIELS-ALDER REACTION; ASYMMETRIC CATALYSIS; WATER; BINDING; CARBANIONS; ANIONS;

D O I：

10.1039/c005048b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A kinetic study of DNA-based catalytic enantioselective Friedel-Crafts alkylation and Michael addition reactions showed that DNA affects the rate of these reactions significantly. Whereas in the presence of DNA, a large acceleration was found for the Friedel-Crafts alkylation and a modest acceleration in the Michael addition of dimethyl malonate, a deceleration was observed when using nitromethane as nucleophile. Also, the enantioselectivities proved to be dependent on the DNA sequence. In comparison with the previously reported Diels-Alder reaction, the results presented here suggest that DNA plays a similar role in both cycloaddition and conjugate addition reactions.

引用

页码：3868 / 3873

页数：6

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