Enantioselective α-fluorination of carbonyl compounds:: Organocatalysis or metal catalysis?

被引：181

作者：

Pihko, PM ^{[1
]}

机构：

[1] Helsinki Univ Technol, Dept Chem Technol, Organ Chem Lab, Helsinki 02015, Finland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 04期

关键词：

alclehydes; asymmetric catalysis; electrophilic substitution; fluorination; organocatalysis;

D O I：

10.1002/anie.200502425

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Five ground-breaking studies in enantioselective α-fluorination of carbonyl compounds have been disclosed. Four describe the use of amine organocatalysts to promote the asymmetric fluorination of aldehydes, whereas the fifth describes a highly enantioselective fluorination of carbonyl compounds capable of two-point binding (e.g. β-ketoesters). NFSI = N-fluorobenzenesulfonimide. (Chemical Equation Presented). © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：544 / 547

页数：4

共 45 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] 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
[3] CU JA, 2004, TETRAHEDRON-ASYMMETR, V15, P1007
[4] Dalko P.I., 2004, ANGEW CHEM, V116, P5248, DOI DOI 10.1002/ANGE.200400650
[5] In the golden age of organocatalysis
Dalko, PI
Moisan, L
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) : 5138 - 5175
[6] Nonracemic alpha-fluoro aldehydes: Asymmetric synthesis of 4-deoxy-4-fluoro-D-arabinopyranose
Davis, FA
Kasu, PVN
Sundarababu, G
Qi, HY
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) : 7546 - 7547
[7] DIFFERDING E, 1991, SYNLETT, P187
[8] Direct organocatalytic α-fluorination of aldehydes and ketones
Enders, D
Hüttl, MRM
[J]. SYNLETT, 2005, (06) : 991 - 993
[9] 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
[10] An efficient enantioselective fluorination of various β-ketoesters catalyzed chiral palladium complexes
Hamashima, Y
Yagi, K
Takano, H
Tamás, L
Sodeoka, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (49) : 14530 - 14531

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