Highly enantioselective catalytic fluorination and chlorination reactions of carbonyl compounds capable of two-point binding

被引：294

作者：

Shibata, N ^{[1
]}

Kohno, J

Takai, K

Ishimaru, T

Nakamura, S

Toru, T

Kanemasa, S

机构：

[1] Nagoya Inst Technol, Grad Sch Engn, Dept Appl Chem, Showa Ku, Nagoya, Aichi 4668555, Japan

[2] Kyushu Univ, Inst Mat Chem & Engn, Kasuga 8168580, Japan

[3] Nagoya Inst Technol, Grad Sch Engn, Dept Appl Chem, Showa Ku, Nagoya, Aichi 4668555, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 27期

关键词：

asymmetric amplification; asymmetric synthesis; enantioselectivity; fluorination; halogenation;

D O I：

10.1002/anie.200501041

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) New tools in drug development: The catalytic enantioselective fluorination and chlorination reactions of carbonyl compounds containing an additional binding site (see scheme) proceed with extremely high enantioselectivity and require low catalyst loadings (2-10 mol% dbfox-Ph/ NiII). Asymmetric amplification is also observed in these enantioselective halogenations. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：4204 / 4207

页数：4

共 51 条

[1] Enantioselective chlorination and fluorination of β-keto phosphonates catalyzed by chiral Lewis acids
Bernardi, L
Jorgensen, KA
[J]. CHEMICAL COMMUNICATIONS, 2005, (10) : 1324 - 1326
[2] 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
[3] Design, synthesis, and evaluation of a novel class of enantioselective electrophilic fluorinating agents:: N-fluoro ammonium salts of cinchona alkaloids (F-CA-BF4)
Cahard, D
Audouard, C
Plaquevent, JC
Roques, N
[J]. ORGANIC LETTERS, 2000, 2 (23) : 3699 - 3701
[4] Asymmetric fluorination of enolates with nonracemic N-fluoro-2,10-camphorsultams
Davis, FA
Zhou, P
Murphy, CK
Sundarababu, G
Qi, HY
Han, W
Przeslawski, RM
Chen, BC
Carroll, PJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (07) : 2273 - 2280
[5] β-keto-ester chemistry and ketolides.: Synthesis and antibacterial activity of 2-halogeno, 2-methyl and 2,3 enol-ether ketolides
Denis, A
Bretin, F
Fromentin, C
Bonnet, A
Piltan, G
Bonnefoy, A
Agouridas, C
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (17) : 2019 - 2022
[6] Filler R., 1982, BIOMEDICAL ASPECTS F
[7] 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
[8] Catalytic, asymmetric α-chlorination of acid halides
France, S
Wack, H
Taggi, AE
Hafez, AM
Wagerle, TR
Shah, MH
Dusich, CL
Lectka, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) : 4245 - 4255
[9] Regio- and enantioselective synthesis of allylic fluorides by electrophilic fluorodesilylation of allyl silanes
Greedy, B
Paris, JM
Vidal, T
Gouverneur, V
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (28) : 3291 - 3294
[10] Greedy B., 2003, ANGEW CHEM, V115, P3413

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