Synthesis of functionalised phenylalanines using rhodium catalysis in water

被引:26
作者
Chapman, CJ [1 ]
Frost, CG [1 ]
机构
[1] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England
关键词
arylation; boronic acids; C-C coupling; conjugate addition; rhodium;
D O I
10.1002/adsc.200390039
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The efficient synthesis of substituted phenylalanine-type amino acids using a rhodium-catalysed, conjugate addition of arylboronic acids is described. The reactions are run in water and use a low loading (0.5 mol %) of rhodium catalyst.
引用
收藏
页码:353 / 355
页数:3
相关论文
共 34 条
[1]   ALKYL AND ARYL COMPLEXES OF IRIDIUM AND RHODIUM .19. REACTION OF CARBOXYLIC-ACIDS WITH SELECTED ORGANO COMPOUNDS OF IR(I) AND RH(I) - FORMATION OF ARYLHYDRIDO, CARBOXYLATOHYDRIDO, AND CARBOXYLATO DERIVATIVES [J].
ARPAC, E ;
MIRZAEI, F ;
YARDIMCIOGLU, A ;
DAHLENBURG, L .
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1984, 519 (12) :148-154
[2]  
Bakos K, 2001, LETT PEPT SCI, V8, P35
[3]  
BARRETT GC, 1985, CHEM BIOCH AMINO ACI
[4]  
BURK MJ, 1998, CHEMTRACTS ORG CHEM, V11, P787
[5]   Asymmetric synthesis of alpha-amino acids via diastereoselective addition of (R)-pantolactone to their ketenes [J].
Calmes, M ;
Daunis, J ;
Mai, N .
TETRAHEDRON-ASYMMETRY, 1997, 8 (10) :1641-1648
[6]   Rhodium catalysed addition of boronic acids to anhydrides: a new method for the synthesis of ketones [J].
Frost, CG ;
Wadsworth, KJ .
CHEMICAL COMMUNICATIONS, 2001, (22) :2316-2317
[7]  
Fürstner A, 2001, ADV SYNTH CATAL, V343, P343
[8]  
Goossen L. J., 2001, ANGEW CHEM, V113, P3566
[9]   Catalytic cycle of rhodium-catalyzed asymmetric 1,4-addition of organoboronic acids.: Arylrhodium, oxa-π-allylrhodium, and hydroxorhodium intermediates [J].
Hayashi, T ;
Takahashi, M ;
Takaya, Y ;
Ogasawara, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (18) :5052-5058
[10]   Rhodium-catalyzed asymmetric conjugate addition of organoboronic acids to nitroalkenes [J].
Hayashi, T ;
Senda, T ;
Ogasawara, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (43) :10716-10717