(S,S)-1,1-bis-ethoxycarbonyl-2,2-bis-p-tolylsulfinyl ethene: A highly stereoselective but unexpectedly unreactive dienophile in asymmetric Diels-Alder reactions

被引：18
作者：
Carretero, JC
Ruano, JLG
Cabrejas, LMM
机构：
[1] Depto. de Quim. Orgánica, Univ. Autónoma de Madrid, Cantoblanco
来源：
TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 03期
关键词：
D O I：
10.1016/S0957-4166(96)00526-5
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The synthesis and dienophilic behaviour of (S,S)-1,1-bis-ethoxycarbonyl-2,2-bis-p-tolylsulfinyl ethene with cyclic and acyclic dienes is reported. The stereoselectivity is high with cyclopentadiene and complete with acyclic dienes, but its reactivity is unexpectedly low, requiring high pressures (13 Kbar) to evolve into the corresponding adducts or their pyrolytic sulfinyl elimination products. (C) 1997 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：409 / 416
页数：8
相关论文
共 38 条
[1]  
AGGARWAL VK, 1992, SYNLETT, P730
[2]   (1R,3R)-2-METHYLENE-1,3-DITHIOLANE 1,3-DIOXIDE - A HIGHLY REACTIVE AND HIGHLY SELECTIVE CHIRAL KETENE EQUIVALENT [J].
AGGARWAL, VK ;
DRABOWICZ, J ;
GRAINGER, RS ;
GULTEKIN, Z ;
LIGHTOWLER, M ;
SPARGO, PL .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (16) :4962-4963
[3]   DIELS-ALDER REACTION OF (S)-2-P-TOLYLSULFINYL-2-CYCLOPENTENONE WITH DANES DIENE - AN EFFICIENT APPROACH TO THE ENANTIOSELECTIVE PREPARATION OF PERHYDRO-CYCLOPENTA[A]PHENANTHRENES [J].
ALONSO, I ;
CARRETERO, JC ;
RUANO, JLG ;
CABREJAS, LMM ;
LOPEZSOLERA, I ;
RAITHBY, PR .
TETRAHEDRON LETTERS, 1994, 35 (50) :9461-9464
[4]   BENZYL METHYL (S)-2-(P-TOLYLSULFINYL)MALEATE, AN EFFICIENT DIENOPHILE IN ASYMMETRIC DIELS-ALDER REACTIONS [J].
ALONSO, I ;
CARRETERO, JC ;
RUANO, JLG .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (06) :1499-1508
[5]  
ARAI T, 1994, J CHEM SOC P1, P25
[6]   ENANTIOSELECTIVE SYNTHESIS OF (+)-INDOLIZIDINE, (+)-LABURNINE AND (+)-ELAEOKANINES A AND C USING THE DIELS-ALDER REACTION OF ALPHA-(2-EXO-HYDROXY-10-BORNYLSULFINYL)MALEIMIDE [J].
ARAI, Y ;
KONTANI, T ;
KOIZUMI, T .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (01) :15-23
[7]   DIMETHYL (R)S-2-(10-ISOBORNYLSULFINYL)MALEATE, A CHIRAL SYNTHETIC EQUIVALENT OF DIMETHYL ACETYLENEDICARBOXYLATE - PREPARATION AND ITS APPLICATION TO THE FORMAL CHIRAL SYNTHESIS OF (-)-NEPLANOCIN A AND (-)-ARISTEROMYCIN [J].
ARAI, Y ;
HAYASHI, K ;
KOIZUMI, T ;
SHIRO, M ;
KURIYAMA, K .
TETRAHEDRON LETTERS, 1988, 29 (47) :6143-6146
[8]  
ARAI Y, 1988, CHEM PHARM BULL, V36, P4162
[9]   A NEW ROUTE TO (-)-ARISTEROMYCIN AND (-)-NEPLANOCIN-A VIA THE ASYMMETRIC DIELS-ALDER CYCLOADDITION [J].
ARAI, Y ;
HAYASHI, Y ;
YAMAMOTO, M ;
TAKAYAMA, H ;
KOIZUMI, T .
CHEMISTRY LETTERS, 1987, (01) :185-186
[10]   OPTICALLY-ACTIVE 2-PARA-TOLYLSULFINYLACRYLATE - A NOVEL CHIRAL DIENOPHILE WHICH EXHIBITS HIGH REACTIVITY AND DIASTEREOSELECTIVITY [J].
ARAI, Y ;
KUWAYAMA, S ;
TAKEUCHI, Y ;
KOIZUMI, T .
TETRAHEDRON LETTERS, 1985, 26 (50) :6205-6208
1234