The Holy Grail of Organocatalysis: Intermolecular α-Alkylation of Aldehydes

被引：58

作者：

Alba, Andrea-Nekane ^{[1
]}

Viciano, Monica ^{[1
]}

Rios, Ramon ^{[1
]}

机构：

[1] Univ Barcelona, Dept Quim Organ, E-08028 Barcelona, Spain

来源：

CHEMCATCHEM | 2009年 / 1卷 / 04期

关键词：

alkylation; carbocations; enantioselectivity; organocatalysis; synthetic methods; CARBOXYLIC-ACID DERIVATIVES; ASYMMETRIC ALKYLATION; ENANTIOSELECTIVE CYCLOPROPANATION; ALPHA; BETA-UNSATURATED ALDEHYDES; 3-(1-ARYLSULFONYLALKYL) INDOLES; CHIRAL CYCLOPROPANES; CATALYSIS; AMINOCATALYSIS; CHEMISTRY; SOLVENT;

D O I：

10.1002/cctc.200900196

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

This is the cup of a chemist: Organocatalytic intermolecular a-alkylation has been accomplished. The groups of Melchiorre and Cozzi have recently reported the realization of this long-time goal in organocatalysis, by the crucial use of stabilized carbocations. Alkylated products are obtained in good yields and with moderate to good enantioselectivities. © 2009 Wiley-VCH Verlag GmbH& Co. KGaA, Weinheim.

引用

页码：437 / 439

页数：3

共 31 条

[11] ASYMMETRIC ALKYLATION REACTIONS OF CHIRAL IMIDE ENOLATES - A PRACTICAL APPROACH TO THE ENANTIOSELECTIVE SYNTHESIS OF ALPHA-SUBSTITUTED CARBOXYLIC-ACID DERIVATIVES
EVANS, DA
ENNIS, MD
MATHRE, DJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (06) : 1737 - 1739
[12] One-pot organocatalytic domino Michael/α-alkylation reactions:: direct catalytic enantioselective cyclopropanation and cyclopentanation reactions
Ibrahem, Ismail
Zhao, Gui-Ling
Rios, Ramon
Vesely, Jan
Sunden, Henrik
Dziedzic, Pawel
Cordova, Armando
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (26) : 7867 - 7879
[13] Lelais G, 2006, ALDRICHIM ACTA, V39, P79
[14] Melchiorre P., 2008, ANGEW CHEM, V120, P6232, DOI DOI 10.1002/ANGE.200705523
[15] Melchiorre P., 2009, ANGEW CHEM, V121, P1386
[16] Asymmetric aminocatalysis - Gold rush in organic chemistry
Melchiorre, Paolo
Marigo, Mauro
Carlone, Armando
Bartoli, Giuseppe
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (33) : 6138 - 6171
[17] Light in Aminocatalysis: The Asymmetric Intermolecular α-Alkylation of Aldehydes
Melchiorre, Paolo
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (08) : 1360 - 1363
[18] Lithium bromide as a flexible, mild, and recyclable reagent for solvent-free Cannizzaro, Tishchenko, and Meerwein-Ponndorf-Verley reactions
Mojtahedi, Mohammad M.
Akbarzadeh, Elahe
Sharifi, Roholah
Abaee, M. Saeed
[J]. ORGANIC LETTERS, 2007, 9 (15) : 2791 - 2793
[19] Asymmetric enamine catalysis
Mukherjee, Santanu
Yang, Jung Woon
Hoffmann, Sebastian
List, Benjamin
[J]. CHEMICAL REVIEWS, 2007, 107 (12) : 5471 - 5569
[20] Merging photoredox catalysis with organocatalysis: The direct asymmetric alkylation of aldehydes
Nicewicz, David A.
MacMillan, David W. C.
[J]. SCIENCE, 2008, 322 (5898) : 77 - 80

← 1 2 3 4 →