Enhancing the catalytic activity of 4-(dialkylamino)pyridines by conformational fixation

被引：112

作者：

Heinrich, MR ^{[1
]}

Klisa, HS ^{[1
]}

Mayr, H ^{[1
]}

Steglich, W ^{[1
]}

Zipse, H ^{[1
]}

机构：

[1] Univ Munich, Dept Chem, D-81377 Munich, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 39期

关键词：

ab initio calculations; acylation; dimethylaminopyridine; kinetics;

D O I：

10.1002/anie.200352289

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Six times more active than DMAP (1), the tricyclic DMAP analogue 2 catalyzes the acetylation of a tertiary alcohol with acetic anhydride. The experimental results can be rationalized by quantum chemical calculations.

引用

页码：4826 / 4828

页数：3

共 34 条

[1]

[Anonymous], ANGEW CHEM

[2] PROTON-TRANSFER STEPS IN STEGLICH ESTERIFICATION - A VERY PRACTICAL NEW METHOD FOR MACROLACTONIZATION [J].

BODEN, EP ;

KECK, GE .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (13) :2394-2395

[3]

CHAUDHARY SK, 1979, TETRAHEDRON LETT, P99

[4] Nucleophilic chiral amines as catalysts in asymmetric synthesis [J].

France, S ;

Guerin, DJ ;

Miller, SJ ;

Lectka, T .

CHEMICAL REVIEWS, 2003, 103 (08) :2985-3012

[5]

Frisch M. J., 2016, Gaussian, V16

[6] Enantioselective nucleophilic catalysis with "planar-chiral" heterocycles [J].

Fu, GC .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :412-420

[7] AMINOPYRIDINES AS ACYLATION CATALYSTS FOR TERTIARY ALCOHOLS [J].

HASSNER, A ;

KREPSKI, LR ;

ALEXANIAN, V .

TETRAHEDRON, 1978, 34 (14) :2069-2076

[8]

HASSNER A, 1978, TETRAHEDRON LETT, P4475

[9]

HASSNER A, 1995, ENCY REAGENTS ORGANI, V3, P2022

[10] 4-DIALKYLAMINOPYRIDINES AS ACYLATION CATALYSTS .3. ACYLATION OF STERICALLY HINDERED ALCOHOLS [J].

HOFLE, G ;

STEGLICH, W .

SYNTHESIS-INTERNATIONAL JOURNAL OF METHODS IN SYNTHETIC ORGANIC CHEMISTRY, 1972, (11) :619-&

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