α-Hydroxyacids accelerate the Diels-Alder reaction of dibutyl vinylboronate with cyclopentadiene: experimental results and mechanistic insights

被引：8

作者：

Grimblat, N. ^{[1
]}

Sarotti, A. M. ^{[1
]}

Pisano, P. L. ^{[1
]}

Pellegrinet, S. C. ^{[1
]}

机构：

[1] Univ Nacl Rosario, Fac Ciencias Bioquim & Farmaceut, CONICET, Inst Quim Rosario, Suipacha 531, RA-2000 Rosario, Santa Fe, Argentina

来源：

NEW JOURNAL OF CHEMISTRY | 2016年 / 40卷 / 03期

关键词：

ELECTRON CHARGE-DENSITY; CYCLOADDITION ROUTE; BORONIC ESTERS; TARTARIC ACID; SELECTIVITY; ARYLATION;

D O I：

10.1039/c5nj03015c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We have found that alpha-hydroxyacids accelerate the Diels-Alder reaction of dibutyl vinylboronate with cyclopentadiene. When stoichiometric quantities are used, excellent yields are obtained, while catalytic activities are moderate. DFT calculations suggested that the activation of the dienophile occurs by ligand exchange with both functionalities of the alpha-hydroxyacid.

引用

页码：1966 / 1969

页数：4

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