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

被引：26

作者：

ALONSO, I

CARRETERO, JC

RUANO, JLG

CABREJAS, LMM

LOPEZSOLERA, I

RAITHBY, PR

机构：

[1] UNIV AUTONOMA MADRID, DEPT QUIM ORGAN C1, E-28049 MADRID, SPAIN

[2] UNIV CAMBRIDGE, CHEM LAB, CAMBRIDGE CB2 1EW, ENGLAND

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 50期

关键词：

D O I：

10.1016/S0040-4039(00)78571-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactions of (S)-2-p-tolylsulfinyl-2-cyclopentenone with Dane's diene catalyzed by EtAlCl(2) yields adducts easily desulfinylated into optically pure perhydro-cyclopenta[a]phenanthrenes. The endo- (controlled by CO group) and regio- (controlled by the substituent at C-2 of diene) selectivities of the asymmetric Diels-Alder reaction are complete. The pi-facial selectivity is also very high and dependent on both the sulfinyl configuration and the amount of EtAlCL(2) used.

引用

收藏

页码：9461 / 9464

页数：4

相关论文

共 27 条

[1] HIGHLY DIASTEREOSELECTIVE DIELS-ALDER REACTION OF OPTICALLY-ACTIVE 2-PARA-TOLYLSULPHINYL-2-CYCLOALKENONES WITH CYCLOPENTADIENE [J].

ALONSO, I ;

CARRETERO, JC ;

RUANO, JLG .

TETRAHEDRON LETTERS, 1989, 30 (29) :3853-3856

[2] SYNTHESIS AND DIELS-ALDER REACTIONS OF HOMOCHIRAL 2-SULFINYLMALEATES WITH CYCLOPENTADIENE [J].

ALONSO, I ;

CID, MB ;

CARRETERO, JC ;

RUANO, JLG ;

HOYOS, MA .

TETRAHEDRON-ASYMMETRY, 1991, 2 (12) :1193-1207

[3] 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

[4] SYNTHESIS AND DIELS-ALDER REACTIONS OF TERT-BUTYL AND TERT-BUTYL, METHYL (S)S-2-PARA-TOLYLSULFINYLMALEATES, CHIRAL SYNTHETIC EQUIVALENTS OF MONOALKYL AND MIXED DIALKYL ACETYLENEDICARBOXYLATES [J].

ALONSO, I ;

CARRETERO, JC ;

RUANO, JLG .

TETRAHEDRON LETTERS, 1991, 32 (07) :947-950

[5] POWERFUL DIENOPHILES FOR ASYMMETRIC DIELS-ALDER REACTIONS - ALPHA-(2-EXO-HYDROXY-10-BORNYLSULFINYL)MALEIMIDES [J].

ARAI, Y ;

MATSUI, M ;

KOIZUMI, T ;

SHIRO, M .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (06) :1983-1985

[6] AN INTRAMOLECULAR DIELS-ALDER APPROACH TO ANGULARLY TRIFLUOROMETHYLATED C/D CIS ESTRANES [J].

BLAZEJEWSKI, JC ;

HADDAD, M ;

WAKSELMAN, C .

TETRAHEDRON LETTERS, 1992, 33 (10) :1269-1272

[7] NOVEL TANDEM REARRANGEMENT OF A STEROIDAL RING-D CYCLOADDUCT DERIVED FROM 2-CHLOROACRYLONITRILE [J].

BULL, JR ;

GRUNDLER, C ;

NIVEN, ML .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (03) :271-273

[8] CONFORMATIONAL DEFORMATION OF RING C IN 14-BETA-ESTRA-1,3,5(10),15-TETRAEN-17-ONES [J].

BULL, JR ;

DILLEN, JLM ;

SEFTON, MA .

TETRAHEDRON, 1990, 46 (24) :8143-8152

[9] CRYSTAL AND MOLECULAR-STRUCTURES OF 3 POLYMORPHIC FORMS OF EXTRONE [J].

BUSETTA, B ;

COURSEILLE, C ;

HOSPITAL, M .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE CRYSTAL ENGINEERING AND MATERIALS, 1973, 29 (FEB15) :298-313

[10]

Dane E, 1938, LIEBIGS ANN CHEM, V536, P196