Palladium-catalysed asymmetric allylic substitution: Synthesis of alpha- and beta-amino acids

被引:98
作者
Bower, JF
Jumnah, R
Williams, AC
Williams, JMJ
机构
[1] UNIV LOUGHBOROUGH,DEPT CHEM,LOUGHBOROUGH LE11 3TU,LEICS,ENGLAND
[2] ELI LILLY & CO,LILLY RES CTR LTD,WINDLESHAM GU20 6PH,SURREY,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 09期
关键词
D O I
10.1039/a606586d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Methodology has been established for the formation of enantiomerically enriched alpha-amino acids using palladium-catalysed allylic amination, The formation of enantiomerically enriched allylamines has been achieved with high enantioselectivity, Oxidative cleavage of the allylamines provides arylglycine and glutamic acid derivatives, Additionally, enantiomerically enriched beta-amino acids have been prepared in high enantiomeric excess, Palladium-catalysed asymmetric allylic substitution is used as the key synthetic transformation.
引用
收藏
页码:1411 / 1420
页数:10
相关论文
共 46 条
[1]   PALLADIUM-CATALYZED ASYMMETRIC ALLYLIC SUBSTITUTION - A LIGAND DESIGN INCORPORATING STERIC AND ELECTRONIC EFFECTS [J].
ALLEN, JV ;
COOTE, SJ ;
DAWSON, GJ ;
FROST, CG ;
MARTIN, CJ ;
WILLIAMS, JMJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (15) :2065-2072
[2]   ASYMMETRIC-SYNTHESIS - ASYMMETRIC CATALYTIC ALLYLATION USING PALLADIUM CHIRAL PHOSPHINE COMPLEXES [J].
AUBURN, PR ;
MACKENZIE, PB ;
BOSNICH, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (07) :2033-2046
[3]   THE PREPARATION OF AMINO-SUGARS AND BRANCHED-CHAIN SUGARS BY PALLADIUM-CATALYZED, ALLYLIC SUBSTITUTION OF ALKYL HEX-2-ENOPYRANOSIDES [J].
BAER, HH ;
HANNA, ZS .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1981, 59 (05) :889-906
[4]   ABSOLUTE CONFIGURATION OF ALPHA-METHYL-BETA-ALANINE [J].
BALENOVIC, K ;
BREGANT, N .
TETRAHEDRON, 1959, 5 (01) :44-47
[5]   OXIDATION OF CYCLOHEXANE BY CERIC AMMONIUM-NITRATE [J].
BRIGUET, C ;
FREPPEL, C ;
RICHERET, JC ;
ZADOR, M .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1974, 52 (18) :3201-3205
[6]   MECHANISTIC AND SYNTHETIC STUDIES IN CATALYTIC ALLYLIC ALKYLATION WITH PALLADIUM COMPLEXES OF 1-(2-DIPHENYLPHOSPHINO-1-NAPHTHYL)ISOQUINOLINE [J].
BROWN, JM ;
HULMES, DI ;
GUIRY, PJ .
TETRAHEDRON, 1994, 50 (15) :4493-4506
[7]   SYNTHESIS OF PROTECTED ALLYLAMINES VIA PALLADIUM-CATALYZED AMIDE ADDITION TO ALLYLIC SUBSTRATES [J].
BYSTROM, SE ;
ASLANIAN, R ;
BACKVALL, JE .
TETRAHEDRON LETTERS, 1985, 26 (14) :1749-1752
[8]   A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].
CARLSEN, PHJ ;
KATSUKI, T ;
MARTIN, VS ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938
[9]   PALLADIUM-CATALYZED SPIROCYCLIZATION OF 3-ACETOXY-1-(4-AMINOALKYL)-CYCLOHEXENES [J].
CARRUTHERS, W ;
MOSES, RC .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (08) :2255-2258
[10]   AN EFFICIENT, PALLADIUM-CATALYZED ROUTE TO PROTECTED ALLYLIC AMINES [J].
CONNELL, RD ;
REIN, T ;
AKERMARK, B ;
HELQUIST, P .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (16) :3845-3849