A convenient cross-coupling route to alpha,beta,gamma,delta-unsaturated amino acids

被引:31
作者
Burk, MJ
Allen, JG
Kiesman, WF
Stoffan, KM
机构
[1] Paul M. Gross Chemical Laboratory, Department of Chemistry, Duke University, Durham
关键词
D O I
10.1016/S0040-4039(97)00065-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
beta-Bromoenamide esters are coupled stereospecifically to vinylboronic acids via a palladium-catalyzed Suzuki reaction. This cross-coupling proceeds under mild conditions with Pd(OAc)(2) in 95% EtOH at 50 degrees C and produces amino acids with 1,3-diene side chains in high yields. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:1309 / 1312
页数:4
相关论文
共 19 条
[2]   Asymmetric catalytic routes to chiral building blocks of medicinal interest [J].
Burk, MJ ;
Gross, MF ;
Harper, TGP ;
Kalberg, CS ;
Lee, JR ;
Martinez, JP .
PURE AND APPLIED CHEMISTRY, 1996, 68 (01) :37-44
[3]   A VERSATILE TANDEM CATALYSIS PROCEDURE FOR THE PREPARATION OF NOVEL AMINO-ACIDS AND PEPTIDES [J].
BURK, MJ ;
LEE, JR ;
MARTINEZ, JP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (23) :10847-10848
[4]   HIGH YIELDS OF UNSYMMETRICAL BIARYLS VIA CROSS-COUPLING OF ARYLBORONIC ACIDS WITH HALOARENES USING A MODIFIED SUZUKI-BELETSKAYA PROCEDURE [J].
CAMPI, EM ;
JACKSON, WR ;
MARCUCCIO, SM ;
NAESLUND, CGM .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (20) :2395-2395
[5]   SYNTHESIS AND REACTIVITY OF PROTECTED BETA-BROMO ALPHA-IMINOACIDS - A CONVENIENT ROUTE TO STRUCTURALLY DIVERSIFIED AMINO-ACIDS [J].
DANIONBOUGOT, R ;
DANION, D ;
FRANCIS, G .
TETRAHEDRON LETTERS, 1990, 31 (26) :3739-3742
[6]   THE SOLUTION STRUCTURE OF THE LANTIBIOTIC GALLIDERMIN [J].
FREUND, S ;
JUNG, G ;
GUTBROD, O ;
FOLKERS, G ;
GIBBONS, WA ;
ALLGAIER, H ;
WERNER, R .
BIOPOLYMERS, 1991, 31 (06) :803-811
[7]  
HEGEDUS L, 1994, ORGANOMETALLICS SYNT, pCH5
[8]  
Jain R, 1996, BIOPOLYMERS, V40, P105, DOI 10.1002/(SICI)1097-0282(1996)40:1<105::AID-BIP5>3.0.CO
[9]  
2-#
[10]   LANTIBIOTICS - RIBOSOMALLY SYNTHESIZED BIOLOGICALLY-ACTIVE POLYPEPTIDES CONTAINING SULFIDE BRIDGES AND ALPHA-BETA-DIDEHYDROAMINO ACIDS [J].
JUNG, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1991, 30 (09) :1051-1068