Kinetics and mechanism of organocatalytic aza-Michael additions: direct observation of enamine intermediates

被引：14

作者：

Lakhdar, Sami ^{[1
]}

Baidya, Mahiuddin ^{[1
]}

Mayr, Herbert ^{[1
]}

机构：

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

来源：

CHEMICAL COMMUNICATIONS | 2012年 / 48卷 / 37期

关键词：

PROLINOL ETHER ENAMINES; ORGANIC CATALYSIS; NUCLEOPHILICITY; SCALES; HETEROCYCLES; STRATEGIES; ADVENT;

D O I：

10.1039/c2cc31224g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The imidazoles 1a-g add to the CC-double bond of the iminium ion 2 with rate constants as predicted by the equation log k = s(N)(N + E). Unfavourable proton shifts from the imidazolium unit to the enamine fragment in the adduct 3 account for the failure of imidazoles to take part in iminium-activated aza-Michael additions to enals.

引用

页码：4504 / 4506

页数：3

共 32 条

[1] New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction
Ahrendt, KA
Borths, CJ
MacMillan, DWC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) : 4243 - 4244
[2] THE APPLICATION OF THE MARCUS RELATION TO REACTIONS IN SOLUTION
ALBERY, WJ
[J]. ANNUAL REVIEW OF PHYSICAL CHEMISTRY, 1980, 31 : 227 - 263
[3] Organocatalytic asymmetric conjugate additions
Almasi, Diana
Alonso, Diego A.
Najera, Carmen
[J]. TETRAHEDRON-ASYMMETRY, 2007, 18 (03) : 299 - 365
[4] Nucleophilicities and Lewis basicities of imidazoles, benzimidazoles, and benzotriazoles
Baidya, Mahiuddin
Brotzel, Frank
Mayr, Herbert
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (08) : 1929 - 1935
[5] Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[6] Brazier JB, 2009, TOP CURR CHEM, V291, P281, DOI [10.1007/128_2008_28, 10.1007/978-3-642-02815-1_28]
[7] Nucleophilicities and carbon basicifies of pyridines
Brotzel, Frank
Kempf, Bernhard
Singer, Thomas
Zipse, Hendrik
Mayr, Herbert
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (01) : 336 - 345
[8] Influence of the Organocatalyst in the Aldol/Mannich-Type Product Selectivities in C-C Bond Forming Reactions
de Maria, Pablo Dominguez
Bracco, Paula
Castelhano, Luiz Fernando
Bargeman, Gerrald
[J]. ACS CATALYSIS, 2011, 1 (02): : 70 - 75
[9] Enantioselective organocatalytic conjugate addition of N heterocycles to α,β-unsaturated aldehydes
Diner, Peter
Nielsen, Martin
Marigo, Mauro
Jorgensen, Karl Anker
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (12) : 1983 - 1987
[10] Organocatalytic Asymmetric Aza-Michael Additions
Enders, Dieter
Wang, Chuan
Liebich, Jens X.
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (42) : 11058 - 11076

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