Organocatalytic asymmetric α-halogenation of 1,3-dicarbonyl compounds

被引：97

作者：

Bartoli, G ^{[1
]}

Bosco, M ^{[1
]}

Carlone, A ^{[1
]}

Locatelli, M ^{[1
]}

Melchiorre, P ^{[1
]}

Sambri, L ^{[1
]}

机构：

[1] Univ Bologna, Alma Mater Studiorum, Dept Organ Chem A Mangini, I-40136 Bologna, Italy

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 38期

关键词：

asymmetric catalysis; 1,3-dicarbonyl compounds; electrophilic substitution; halogenation; organcatalysis;

D O I：

10.1002/anie.200502134

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) No metal required: A protocol for the enantioselective organocatalytic chlorination of cyclic and acyclic β-keto esters and cyclic β-diketones has been developed which is also effective for the asymmetric bromination of β-keto esters. The methodology employs an inexpensive organocatalyst (e.g. benzoylquinidine) and polyhalogenated quinolinones as the source of the halogen (see scheme). © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：6219 / 6222

页数：4

共 39 条

[1] Enantioselective organocatalytic α-fluorination of aldehydes
Beeson, TD
MacMillan, DWC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (24) : 8826 - 8828
[2] Organocatalytic enantioselective conjugate addition to alkynones
Bella, M
Jorgensen, KA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (18) : 5672 - 5673
[3] Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[4] BERKESSEL A, 2004, ACC CHEM RES, V37
[5] Enantioselective chlorination and fluorination of β-keto phosphonates catalyzed by chiral Lewis acids
Bernardi, L
Jorgensen, KA
[J]. CHEMICAL COMMUNICATIONS, 2005, (10) : 1324 - 1326
[6] Direct and enantioselective organocatalytic α-chlorination of aldehydes
Brochu, MP
Brown, SP
MacMillan, DWC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) : 4108 - 4109
[7] Dalko P.I., 2004, ANGEW CHEM, V116, P5248, DOI DOI 10.1002/ANGE.200400650
[8] In the golden age of organocatalysis
Dalko, PI
Moisan, L
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) : 5138 - 5175
[9] DEKIMPE N, 1990, ALPHA HALOKETONES AL
[10] Recent developments in catalytic, asymmetric α-halogenation:: A new frontier in asymmetric catalysis
France, S
Weatherwax, A
Lectka, T
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (03) : 475 - 479

← 1 2 3 4 →