Ruthenium(II) in ring closing metathesis for the stereoselective preparation of cyclic 1-amino-1-carboxylic acids.

被引:77
作者
Hammer, K [1 ]
Undheim, K [1 ]
机构
[1] UNIV OSLO, DEPT CHEM, N-0315 OSLO, NORWAY
关键词
D O I
10.1016/S0040-4020(96)01132-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Stereoselective synthesis of alpha-amino acids where the alpha-carbon of the amino acid is incorporated into a five-, six- or seven-membered ring is described. The stereoselective control results from stepwise bisalkenylation of (R)-25-dihydro-3,6-dimethoxy-2-isopropylpyrazine. Ring closing metathesis was effected by ruthenium(II)-catalysis. The spiro-cycloalkene intermediates were further transformed into 1-aminocycloalkene-1-carboxylic acid derivatives by mild add hydrolysis. (C) 1997, Elsevier Science Ltd.
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页码:2309 / 2322
页数:14
相关论文
共 42 条
[1]   SYNTHESIS OF 3-SUBSTITUTED AND 4-SUBSTITUTED CYCLIC ALPHA-AMINO-ACIDS STRUCTURALLY RELATED TO ACPD [J].
ALONSO, F ;
MICO, I ;
NAJERA, C ;
SANSANO, JM ;
YUS, M ;
EZQUERRA, J ;
YRURETAGOYENA, B ;
GRACIA, I .
TETRAHEDRON, 1995, 51 (37) :10259-10280
[2]   CONFORMATIONALLY CONSTRAINED AMINO-ACIDS - SYNTHESIS AND OPTICAL RESOLUTION OF 3-SUBSTITUTED PROLINE DERIVATIVES [J].
CHUNG, JYL ;
WASICAK, JT ;
ARNOLD, WA ;
MAY, CS ;
NADZAN, AM ;
HOLLADAY, MW .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) :270-275
[3]   Asymmetric cyclopropanations by rhodium(II) N-(arylsulfonyl)prolinate catalyzed decomposition of vinyldiazomethanes in the presence of alkenes. Practical enantioselective synthesis of the four stereoisomers of 2-phenylcyclopropan-1-amino acid [J].
Davies, HML ;
Bruzinski, PR ;
Lake, DH ;
Kong, N ;
Fall, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (29) :6897-6907
[4]  
DEGRADO WF, 1988, ADV PROTEIN CHEM, V39, P51
[5]   CONFORMATIONALLY CONSTRAINED ACPD ANALOGS - SYNTHESIS AND RESOLUTION OF 3-AMINOBICYCLO[3,3,0]OCTANE-1,3-DICARBOXYLIC ACIDS [J].
EZQUERRA, J ;
YRURETAGOYENA, B ;
AVENDANO, C ;
DELACUESTA, E ;
GONZALEZ, R ;
PRIETO, L ;
PEDREGAL, C ;
ESPADA, M ;
PROWSE, W .
TETRAHEDRON, 1995, 51 (11) :3271-3278
[6]   Asymmetric synthesis of phenylbis(glycines) [J].
FalckPedersen, ML ;
Undheim, K .
TETRAHEDRON, 1996, 52 (22) :7761-7770
[7]   CATALYTIC RING-CLOSING METATHESIS OF FUNCTIONALIZED DIENES BY A RUTHENIUM CARBENE COMPLEX [J].
FU, GC ;
NGUYEN, ST ;
GRUBBS, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (21) :9856-9857
[8]   THE APPLICATION OF CATALYTIC RING-CLOSING OLEFIN METATHESIS TO THE SYNTHESIS OF UNSATURATED OXYGEN HETEROCYCLES [J].
FU, GC ;
GRUBBS, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :5426-5427
[9]   THE SYNTHESIS OF CYCLIC ENOL ETHERS VIA MOLYBDENUM ALKYLIDENE-CATALYZED RING-CLOSING METATHESIS [J].
FUJIMURA, O ;
FU, GC ;
GRUBBS, RH .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (15) :4029-4031
[10]   PEPTIDOMIMETICS FOR RECEPTOR LIGANDS DISCOVERY, DEVELOPMENT, AND MEDICAL PERSPECTIVES [J].
GIANNIS, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1993, 32 (09) :1244-1267