Synthesis of γ,δ-didehydrohomoglutamates by the phosphine-catalyzed γ-addition reaction to acetylenic esters

被引:38
作者
Alvarez-Ibarra, C [1 ]
Csáky, AG [1 ]
de la Oliva, CG [1 ]
机构
[1] Univ Complutense, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
关键词
D O I
10.1021/jo9918192
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
引用
收藏
页码:3544 / 3547
页数:4
相关论文
共 42 条
[1]   Carboxylates as pronucleophiles in the phosphine-catalyzed γ-addition reaction [J].
Alvarez-Ibarra, C ;
Csáky, AG ;
de la Oliva, CG .
TETRAHEDRON LETTERS, 1999, 40 (48) :8465-8467
[2]   Reaction of N-[bis(methylthio)methylene]glycinates with electron deficient alkynes, synthesis of (Z)-alpha,beta-didehydroglutamic acid derivatives [J].
AlvarezIbarra, C ;
Csaky, AG ;
Ortega, EM ;
delaMorena, MJ ;
Quiroga, ML .
TETRAHEDRON LETTERS, 1997, 38 (25) :4501-4502
[3]   Asymmetric oxidative dimerization of the enolates of N-[bis(methylthio)methylene]- and N-(diphenylmethylene)glycine esters [J].
AlvarezIbarra, C ;
Csaky, AG ;
Colmenero, B ;
Quiroga, ML .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) :2478-2482
[4]   STEREOSELECTIVE SYNTHESIS OF THE DIHYDROXYISOLEUCINE CONSTITUENT OF THE AMANITA MUSHROOM TOXINS [J].
BARTLETT, PA ;
TANZELLA, DJ ;
BARSTOW, JF .
TETRAHEDRON LETTERS, 1982, 23 (06) :619-622
[5]   BIOSYNTHESIS OF PORPHYRINS AND RELATED MACROCYCLES .29. SYNTHESIS AND CHEMISTRY OF 2,2-DISUBSTITUTED 2H-PYRROLES (PYRROLENINES) [J].
BATTERSBY, AR ;
BAKER, MG ;
BROADBENT, HA ;
FOOKES, CJR ;
LEEPER, FJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (09) :2027-2048
[6]   SYNTHESIS OF ETHYL (2RS,3SR)-1-TOSYL-3-VINYLAZETIDINE-2-CARBOXYLATE AND ETHYL (2RS,E)-3-ETHYLIDENE-1-TOSYLAZETIDINE-2-CARBOXYLATE (= RAC-ETHYL N-TOSYLPOLYOXIMATE) [J].
BAUMANN, H ;
DUTHALER, RO .
HELVETICA CHIMICA ACTA, 1988, 71 (05) :1025-1034
[7]   SYNTHESIS OF (OPTICALLY-ACTIVE) SULFUR-CONTAINING TRIFUNCTIONAL AMINO-ACIDS BY RADICAL-ADDITION TO (OPTICALLY-ACTIVE) UNSATURATED AMINO-ACIDS [J].
BROXTERMAN, QB ;
KAPTEIN, B ;
KAMPHUIS, J ;
SCHOEMAKER, HE .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (23) :6286-6294
[8]   CONFORMATIONAL EFFECTS OF SUBSTITUTING METHIONINE WITH (2S,3S)-2,3-METHANOMETHIONINE IN PHE-MET-ARG-PHE-NH2 [J].
BURGESS, K ;
HO, KK ;
PETTITT, BM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (01) :54-65
[9]   Highly regio- and enantioselective catalytic hydrogenation of enamides in conjugated diene systems:: Synthesis and application of γ,δ-unsaturated amino acids [J].
Burk, MJ ;
Allen, JG ;
Kiesman, WF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (04) :657-663
[10]   Asymmetric synthesis of alpha-methyl alpha-amino acids by diastereoselective alkylation of optically active 6-isopropyl-3-methyl-2,3-dihydro-6H-1,4-oxazin-2-ones [J].
Chinchilla, R ;
Falvello, LR ;
Galindo, N ;
Najera, C .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (09) :995-997