Pd-catalyzed cyclization reactions of acetylene-containing α-amino acids

被引:56
作者
Wolf, LB
Tjen, KCMF
Rutjes, FPJT
Hiemstra, H
Schoemaker, HE
机构
[1] Univ Amsterdam, Inst Mol Chem, Organ Chem Lab, NL-1018 WS Amsterdam, Netherlands
[2] DSM Res, NL-6160 MD Geleen, Netherlands
关键词
amino acids and derivatives; Pd-catalysis; enamino esters; cyclization;
D O I
10.1016/S0040-4039(98)00910-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Acetylene-containing amino acids, obtained in enantiopure form via an enzymatic resolution process, serve as versatile intermediates in the synthesis of various highly functionalized heterocycles. The key transformations, intramolecular OC- and NC-bond formation, proceed via Pd-catalysis. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5081 / 5084
页数:4
相关论文
共 19 条
[1]  
Arcadi A, 1997, SYNLETT, P941
[2]   PALLADIUM-CATALYZED REACTION OF VINYL TRIFLATES AND VINYL ARYL HALIDES WITH 4-ALKYNOIC ACIDS - REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF (E)-DELTA-VINYL ARYL-GAMMA-METHYLENE-GAMMA-BUTYROLACTONES [J].
ARCADI, A ;
BURINI, A ;
CACCHI, S ;
DELMASTRO, M ;
MARINELLI, F ;
PIETRONI, BR .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (03) :976-982
[3]  
BOESTEN WHJ, 1987, Patent No. 4705752
[4]  
Bouyssi D, 1997, SYNLETT, P944
[5]   KINETIC RESOLUTION OF UNNATURAL AND RARELY OCCURRING AMINO-ACIDS - ENANTIOSELECTIVE HYDROLYSIS OF N-ACYL AMINO-ACIDS CATALYZED BY ACYLASE-I [J].
CHENAULT, HK ;
DAHMER, J ;
WHITESIDES, GM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) :6354-6364
[6]   PALLADIUM-CATALYZED INTRAMOLECULAR ADDITION OF AMINES TO ACETYLENES - SYNTHESIS OF CYCLIC IMINES [J].
FUKUDA, Y ;
MATSUBARA, S ;
UTIMOTO, K .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5812-5816
[7]  
GRIBBLE GW, 1997, PROGR HETEROCYCLIC C, V9
[8]   Photochemistry of N-phthaloylcysteine derivatives: Multiplicity-directed regioselective CH activation [J].
Griesbeck, AG ;
Hirt, J ;
Peters, K ;
Peters, EM ;
vonSchnering, HG .
CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (11) :1388-1394
[9]  
Kotora M., 1996, SYNTHESIS-STUTTGART, P121
[10]   PALLADIUM(II) CATALYZED CYCLIZATION OF ALKYNOIC ACIDS [J].
LAMBERT, C ;
UTIMOTO, K ;
NOZAKI, H .
TETRAHEDRON LETTERS, 1984, 25 (46) :5323-5326