Enantioselective halogenation reactions

被引:229
作者
Ibrahim, H [1 ]
Togni, A [1 ]
机构
[1] ETH Honggerberg, Swiss Fed Inst Technol, Dept Chem & Appl Biosci, CH-8093 Zurich, Switzerland
关键词
D O I
10.1039/b317004g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Stereoselective halogenation reactions, in particular fluorinations, are not everyday's chemistry despite the fundamental and still increasing significance of fluorinated molecules, e.g., for the life science industry. The selective fluorination of a bioactive compound can be generally beneficial in terms of a possible increased intrinsic activity, enhanced chemical and metabolic stability, and improved pharmacokinetics. It is clear that more efficient and selective methodologies for the introduction of fluorine into organic molecules are still needed. We review in this article latest progresses in the area of enantioselective fluorinations, with particular emphasis on new catalytic reactions and extend our discussion to similar reactions involving the other halogens.
引用
收藏
页码:1147 / 1155
页数:9
相关论文
共 75 条
[1]   N-HALOGENO COMPOUNDS .14. TRANSFER FLUORINATION OF QUINUCLIDINE USING F-TEDA-BF4 (SELECTOR(TM) REAGENT) - LABORATORY SYNTHESIS OF N-FLUOROQUINUCLIDINIUM SALTS NOT REQUIRING THE USE OF ELEMENTAL FLUORINE [J].
ABDULGHANI, M ;
BANKS, RE ;
BESHEESH, MK ;
SHARIF, I ;
SYVRET, RG .
JOURNAL OF FLUORINE CHEMISTRY, 1995, 73 (02) :255-257
[2]   Selectfluor™ reagent F-TEDA-BF4 in action:: Tamed fluorine at your service [J].
Banks, RE .
JOURNAL OF FLUORINE CHEMISTRY, 1998, 87 (01) :1-17
[3]   EFFICIENT ELECTROPHILIC FLUORINATION OF BETA-DICARBONYL COMPOUNDS WITH THE SELECTFLUOR REAGENT F-TEDA-BF4 (1-CHLOROMETHYL-4-FLUORO-1,4-DIAZONIABICYCLO[2.2.2]OCTANE BIS(TETRAFLUOROBORATE)) [J].
BANKS, RE ;
LAWRENCE, NJ ;
POPPLEWELL, AL .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (03) :343-344
[4]   Catalytic fluorination by halide exchange with 16-electron ruthenium(II) complexes.: X-ray structure of [Tl(μ-F)2Ru(dppe)2]PF6 [J].
Barthazy, P ;
Togni, A ;
Mezzetti, A .
ORGANOMETALLICS, 2001, 20 (16) :3472-3477
[5]   Enantioselective electrophilic fluorination: a study of the fluorine-transfer from achiral N-F reagents to cinchona alkaloids [J].
Baudequin, C ;
Loubassou, JF ;
Plaquevent, JC ;
Cahard, D .
JOURNAL OF FLUORINE CHEMISTRY, 2003, 122 (02) :189-193
[6]   Enantioselective electrophilic fluorination in ionic liquids [J].
Baudequin, C ;
Plaquevent, JC ;
Audouard, C ;
Cahard, D .
GREEN CHEMISTRY, 2002, 4 (06) :584-586
[7]   Synthesis of novel chiral quaternary phosphonium fluorides: reagents for simple asymmetric nucleophilic fluorination reactions [J].
Beaumont, AJ ;
Kiely, C ;
Rooney, AD .
JOURNAL OF FLUORINE CHEMISTRY, 2001, 108 (01) :47-50
[8]  
BECKER C, UNPUB
[9]   Electronic tuning of the PNNP ligand for the asymmetric cyclopropanation of olefins catalysed by [RuCl(PNNP)] [J].
Bonaccorsi, C ;
Bachmann, S ;
Mezzetti, A .
TETRAHEDRON-ASYMMETRY, 2003, 14 (07) :845-854
[10]   Enantioselective introduction of fluoride into organic compounds First asymmetric ring opening of epoxides by hydrofluorinating reagents [J].
Bruns, S ;
Haufe, G .
JOURNAL OF FLUORINE CHEMISTRY, 2000, 104 (02) :247-254