CAPTODATIVE ALPHA,BETA-UNSATURATED OXAZOLINES AS DIENOPHILES IN THE ASYMMETRIC DIELS-ALDER REACTION

被引:15
作者
LANGLOIS, Y [1 ]
POUILHES, A [1 ]
机构
[1] CNRS,INST CHIM SUBSTANCES NAT,F-91198 GIF SUR YVETTE,FRANCE
关键词
THERMAL-REACTIONS; CYCLO-ADDITIONS; OLEFINS; ACIDS;
D O I
10.1016/S0957-4166(00)80022-1
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Captodative oxazoline derivative 5a gave rise to four-cycloadducts 6,7,8 and 9 in the presence of trifluoroacetic anhydride and cyclopentadiene. Hydrolysis of 6 led to alpha-phenylthio carboxylic acid 14.
引用
收藏
页码:1223 / 1230
页数:8
相关论文
共 17 条
[1]   AN EFFICIENT AND SHORT DEGRADATION OF THE CHOLIC-ACID SIDE-CHAIN - A NEW METHOD FOR THE PREPARATION AND DEHYDROGENATION OF 4,5-DIHYDRO-OXAZOLES [J].
BARTON, DHR ;
MOTHERWELL, WB ;
WOZNIAK, J ;
ZARD, SZ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (09) :1865-1869
[2]   CAPTODATIVE SUBSTITUENT EFFECTS .32. THE INFLUENCE OF CAPTODATIVE EFFECT ON THE DIENOPHILICITY OF OLEFINS - THE EASY DIELS-ALDER REACTION OF ALPHA-METHYLTHIOACRYLONITRILE WITH CYCLOHEXADIENE [J].
BOUCHER, JL ;
STELLA, L .
TETRAHEDRON LETTERS, 1985, 26 (41) :5041-5044
[3]   DIENOPHILS OF CAPTODATIVE OLEFINS - DIELS-ALDER CYCLOADDITIONS OF ALPHA-METHYLTHIO-ACRYLONITRILE AND ADDUCT TRANSFORMATION [J].
BOUCHER, JL ;
STELLA, L .
TETRAHEDRON, 1986, 42 (14) :3871-3885
[4]   DIENOPHILICITY OF CAPTODATIVE OLEFINS .7. DIELS-ADLER CYCLO-ADDITIONS OF ALPHA-METHYLTHIO METHYL ACRYLATE, THERMAL-REACTIONS, LEWIS ACID-CATALYZED REACTIONS AND TRANSFORMATIONS OF ADDUCTS [J].
BOUCHER, JL ;
STELLA, L .
TETRAHEDRON, 1988, 44 (12) :3607-3615
[5]   A NOVEL PREPARATIVE METHOD FOR ALPHA,BETA-UNSATURATED OXAZOLINES VIA ALPHA-PHENYLTHIOOXAZOLINES [J].
CLINET, JC ;
BALAVOINE, G .
TETRAHEDRON LETTERS, 1987, 28 (45) :5509-5512
[6]   GENERAL PROCEDURE FOR BASE-PROMOTED HYDROLYSIS OF HINDERED ESTERS AT AMBIENT-TEMPERATURES [J].
GASSMAN, PG ;
SCHENK, WN .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (05) :918-920
[7]   ALPHA,BETA-UNSATURATED OXAZOLINES, A POWERFUL TOOL IN ASYMMETRIC DIELS-ALDER CYCLOADDITIONS [J].
KOUKLOVSKY, C ;
POUILHES, A ;
LANGLOIS, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (18) :6672-6679
[8]   SYNTHESIS AND DIELS-ALDER REACTIONS OF (+)-(S)-1-TERT-BUTYLSULFONYL-1-PARA-TOLYLSULFINYLETHENE, A NEW MASKED CHIRAL KETENE EQUIVALENT [J].
LOPEZ, R ;
CARRETERO, JC .
TETRAHEDRON-ASYMMETRY, 1991, 2 (02) :93-96
[9]   A NEW CHIRAL KETENE SYNTHON - A NEW CHIRAL MASKED KETENE SYNTHON, R-(+)-ETHYNYL PARA-TOLYLSULFOXIDE [J].
MAIGNAN, C ;
BELKASMIOUI, F .
TETRAHEDRON LETTERS, 1988, 29 (23) :2823-2824
[10]   THERMAL-REACTIONS OF DONOR-ACCEPTOR SYSTEMS .3. CAPTODATIVE OLEFINS IN NORMAL AND INVERSE DIELS-ALDER REACTIONS [J].
MERTES, J ;
MATTAY, J .
HELVETICA CHIMICA ACTA, 1988, 71 (04) :742-748