SYNTHESIS OF THE 4 D,L-PAIRS OF 2-AMINO-3-PHENYLNORBORNANE-2-CARBOXYLIC ACIDS .2. THE USE OF 5(4H)-OXAZOLONES AS DIENOPHILES

被引:36
作者
CATIVIELA, C [1 ]
DEVILLEGAS, MDD [1 ]
MAYORAL, JA [1 ]
AVENOZA, A [1 ]
PEREGRINA, JM [1 ]
机构
[1] COLEGIO UNIV LA RIOJA,DEPT ORGAN CHEM,E-26001 LOGRONO,SPAIN
关键词
(E)-OXAZOLONES AND (Z)-OXAZOLONES; DIELS-ALDER CYCLOADDITION; ALPHA-AMINO-ACIDS;
D O I
10.1016/S0040-4020(01)86269-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Diels-Alder reaction between both geometric isomers (Z)- or (E)-2-phenyl-4-benzylidene-5(4H)-oxazolone and cyclopentadiene is studied. The cycloadducts are converted into the aminoacids through simple reactions allowing the synthesis of the four d,l-pairs of 2-amino-3-phenylnorbornane-2-carboxylic acids.
引用
收藏
页码:677 / 684
页数:8
相关论文
共 25 条
[1]   SYNTHESIS OF THE 4 DL-PAIRS OF 2-AMINO-3-PHENYLNORBORNANE-2-CARBOXYLIC ACIDS [J].
AVENOZA, A ;
CATIVIELA, C ;
MAYORAL, JA ;
ROY, MA .
TETRAHEDRON, 1989, 45 (12) :3923-3934
[2]   ON THE ORIGIN OF PRODUCT SELECTIVITY IN AQUEOUS DIELS-ALDER REACTIONS [J].
BRESLOW, R ;
MAITRA, U .
TETRAHEDRON LETTERS, 1984, 25 (12) :1239-1240
[3]   SELECTIVE DIELS-ALDER REACTIONS IN AQUEOUS-SOLUTIONS AND SUSPENSIONS [J].
BRESLOW, R ;
MAITRA, U ;
RIDEOUT, D .
TETRAHEDRON LETTERS, 1983, 24 (18) :1901-1904
[4]   DIELS-ALDER REACTIONS OF METHYL-N-ACYL-ALPHA,BETA-DEHYDROALANINATES WITH CYCLOPENTADIENE [J].
BUENO, MP ;
CATIVIELA, C ;
FINOL, C ;
MAYORAL, JA ;
JAIME, C .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1987, 65 (09) :2182-2186
[5]   ETHYL 2-(DIPHENYLMETHYLENEAMINO)ACRYLATE AS A DIENOPHILE IN THE SYNTHESIS OF ALICYCLIC ALPHA-AMINO-ACIDS [J].
CATIVIELA, C ;
FRAILE, JM ;
MAYORAL, JA .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (08) :2456-2457
[6]   ASYMMETRIC-SYNTHESIS OF 2-AMINONORBORNANE-2-CARBOXYLIC ACIDS BY DIELS-ALDER REACTION [J].
CATIVIELA, C ;
LOPEZ, P ;
MAYORAL, JA .
TETRAHEDRON-ASYMMETRY, 1990, 1 (02) :61-64
[7]   ASYMMETRIC-SYNTHESIS OF 2-EXO-AMINONORBORNANE-2-ENDO-CARBOXYLIC ACID-DERIVATIVES [J].
CATIVIELA, C ;
LOPEZ, P ;
MAYORAL, JA .
TETRAHEDRON-ASYMMETRY, 1991, 2 (06) :449-456
[8]  
CATIVIELA C, 1990, SYNTHESIS-STUTTGART, P1114
[9]   ASYMMETRIC-SYNTHESIS OF 2-AMINONORBORNANE-2-CARBOXYLIC ACIDS BY DIELS-ALDER REACTION [J].
CATIVIELA, C ;
LOPEZ, P ;
MAYORAL, JA .
TETRAHEDRON-ASYMMETRY, 1991, 2 (12) :1295-1304
[10]   CORRELATIONS OF RATE AND SELECTIVITY OF A DIELS-ALDER REACTION WITH SP PARAMETERS [J].
CATIVIELA, C ;
MAYORAL, JA ;
AVENOZA, A ;
PEREGRINA, JM ;
ROY, MA .
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 1990, 3 (06) :414-418