Catalytic asymmetric synthesis of tertiary alkyl chlorides

被引：38

作者：

Lee, Elaine C. ^{[1
]}

McCauley, Kevin M. ^{[1
]}

Fu, Gregory C. ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 06期

关键词：

asymmetric catalysis; chlorination; ketenes;

D O I：

10.1002/anie.200604312

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Ketenes are coupled with 2,2,6,6- tetrachlorocyclohexanone in a catalytic asymmetric method for the synthesis of tertiary α-chloroesters (see scheme). This complements recent progress in the generation of secondary α-halocarbonyl compounds. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

收藏

页码：977 / 979

页数：3

相关论文

共 40 条

[1] Organocatalytic asymmetric α-halogenation of 1,3-dicarbonyl compounds [J].

Bartoli, G ;

Bosco, M ;

Carlone, A ;

Locatelli, M ;

Melchiorre, P ;

Sambri, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) :6219-6222

[2]

Bartoli G., 2005, ANGEW CHEM, V117, P6375

[3] Enantioselective chlorination and fluorination of β-keto phosphonates catalyzed by chiral Lewis acids [J].

Bernardi, L ;

Jorgensen, KA .

CHEMICAL COMMUNICATIONS, 2005, (10) :1324-1326

[4] Direct and enantioselective organocatalytic α-chlorination of aldehydes [J].

Brochu, MP ;

Brown, SP ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4108-4109

[5]

De Kimpe N., 1988, ALPHA HALOKETONES AL

[6] Identification of novel mammalian squalene synthase inhibitors using a three-dimensional pharmacophore [J].

Fairlamb, IJS ;

Dickinson, JM ;

O'Connor, R ;

Higson, S ;

Grieveson, L ;

Marin, V .

BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (08) :2641-2656

[7] Recent developments in catalytic, asymmetric α-halogenation:: A new frontier in asymmetric catalysis [J].

France, S ;

Weatherwax, A ;

Lectka, T .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (03) :475-479

[8] Catalytic, asymmetric α-chlorination of acid halides [J].

France, S ;

Wack, H ;

Taggi, AE ;

Hafez, AM ;

Wagerle, TR ;

Shah, MH ;

Dusich, CL ;

Lectka, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4245-4255

[9] Asymmetric catalysis with "planar-chiral" derivatives of 4-(dimethylamino)pyridine [J].

Fu, GC .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :542-547

[10] STUDIES ON NEW ANTIBIOTICS-SF2415 .2. THE STRUCTURAL ELUCIDATION [J].

GOMI, S ;

OHUCHI, S ;

SASAKI, T ;

ITOH, J ;

SEZAKI, M .

JOURNAL OF ANTIBIOTICS, 1987, 40 (06) :740-749

← 1 2 3 4 →