Synthesis of Halogenated Carboxylic Acids and Amino Acids

被引:50
作者
Czekelius, Constantin [1 ]
Tzschucke, Carl Christoph [1 ]
机构
[1] Free Univ Berlin, Inst Chem & Biochem, D-14195 Berlin, Germany
来源
SYNTHESIS-STUTTGART | 2010年 / 04期
关键词
halogens; fluorine; trifluoromethylation; enantioselective methods; organocatalysis; BETA-KETO-ESTERS; CATALYTIC ENANTIOSELECTIVE FLUORINATION; CHIRAL PALLADIUM COMPLEXES; FRIEDEL-CRAFTS ALKYLATION; ASYMMETRIC ELECTROPHILIC FLUORINATION; N-FLUOROAMMONIUM SALTS; SILYL ENOL ETHERS; ORGANOCATALYTIC ALPHA-FLUORINATION; HIGHLY STEREOSELECTIVE-SYNTHESIS; QUATERNARY STEREOGENIC CENTERS;
D O I
10.1055/s-0029-1218649
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学];
摘要
This review summarizes and focuses on stereoselective methods for the preparation of halogenated carboxylic acids and amino acids. Diastereoselective and enantioselective halogen atom transfer processes as well as methods for the synthesis of fluoroalkyl-substituted compounds are discussed in detail.
引用
收藏
页码:543 / 566
页数:24
相关论文
共 231 条
[1]
Ruthenium-catalyzed asymmetric electrophilic fluorination of 1,3-dicarbonyl compounds [J].
Althaus, Martin ;
Becker, Claus ;
Togni, Antonio ;
Mezzetti, Antonio .
ORGANOMETALLICS, 2007, 26 (24) :5902-5911
[2]
Stereoselective synthesis of β-amino-α-fluoro esters via diastereoselective fluorination of enantiopure β-amino enolates [J].
Andrews, PC ;
Bhaskar, V ;
Bromfield, KM ;
Dodd, AM ;
Duggan, PJ ;
Duggan, SAM ;
McCarthy, TD .
SYNLETT, 2004, (05) :791-794
[3]
[Anonymous], 2009, ANGEW CHEM
[4]
2,2′-Bipyridine-3,3′-dicarboxylic carbohydrate esters and amides. Synthesis and preliminary evaluation as ligands in Cu(II)-catalysed enantioselective electrophilic fluorination [J].
Assalit, Aurelie ;
Billard, Thierry ;
Chambert, Stephane ;
Langlois, Bernard R. ;
Queneau, Yves ;
Coe, Diane .
TETRAHEDRON-ASYMMETRY, 2009, 20 (05) :593-601
[5]
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
[6]
SYNTHESIS AND PROPERTIES OF (TRIFLUOROMETHYL)TRICHLOROSILANE, A VERSATILE PRECURSOR FOR CF3SI COMPOUNDS [J].
BECKERS, H ;
BURGER, H ;
BURSCH, P ;
RUPPERT, I .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1986, 316 (1-2) :41-50
[7]
Enantioselective organocatalytic α-fluorination of aldehydes [J].
Beeson, TD ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (24) :8826-8828
[8]
Organocatalytic asymmetric α-bromination of aldehydes and ketones [J].
Bertelsen, S ;
Halland, N ;
Bachmann, S ;
Marigo, M ;
Braunton, A ;
Jorgensen, KA .
CHEMICAL COMMUNICATIONS, 2005, (38) :4821-4823
[9]
Catalytic asymmetric fluorinations [J].
Bobbio, Carla ;
Gouverneur, Veronique .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (11) :2065-2075
[10]
Bogevig A, 2002, CHEM-EUR J, V8, P5652, DOI 10.1002/1521-3765(20021216)8:24<5652::AID-CHEM5652>3.0.CO