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

[1] [Anonymous], 2008, ANGEW CHEM
[2] Reaction of 3-(1-arylsulfonylalkyl)-indoles with easily enolisable derivatives promoted by potassium fluoride on basic alumina
Ballini, Roberto
Palmieri, Alessandro
Petrini, Marino
Shaikh, Rafik R.
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (01) : 129 - 134
[3] Solventless clay-promoted Friedel-Crafts reaction of indoles with α-amido sulfones:: Unexpected synthesis of 3-(1-arylsulfonylalkyl) indoles
Ballini, Roberto
Palmieri, Alessandro
Petrini, Marino
Torregiani, Elisabetta
[J]. ORGANIC LETTERS, 2006, 8 (18) : 4093 - 4096
[4] Organocatalysis - Organocatalysis lost: Modern chemistry, ancient chemistry, and an unseen biosynthetic apparatus
Barbas, Carlos F., III
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (01) : 42 - 47
[5] Asymmetric Organocatalytic Cyclopropanation - Highly Stereocontrolled Synthesis of Chiral Cyclopropanes with Quaternary Stereocenters
Companyo, Xavier
Alba, Andrea-Nekane
Cardenas, Francisco
Moyano, Albert
Rios, Ramon
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (18) : 3075 - 3080
[6] Cozzi P. G., 2009, ANGEW CHEM, V121, P1339
[7] Organocatalytic Asymmetric Alkylation of Aldehydes by SN1-Type Reaction of Alcohols
Cozzi, Pier Giorgio
Benfatti, Fides
Zoli, Luca
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (07) : 1313 - 1316
[8] DEMONMOUTH G, HIST REGUM BRITANNIA, P1130
[9] Enders D., 2008, ANGEW CHEM, V120, P7649, DOI DOI 10.1002/ANGE.200802532
[10] Organocatalytic asymmetric domino reactions:: A cascade consisting of a Michael addition and an aldehyde α-alkylation
Enders, Dieter
Wang, Chuan
Bats, Jan W.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (39) : 7539 - 7542

← 1 2 3 4 →