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

页码：9461 / 9464

页数：4

共 27 条

[21] HIGHLY DIASTEREOSELECTIVE DIELS-ALDER REACTIONS WITH (R)-ETHOXY PARA-TOLY VINYL SULFONIUM TETRAFLUOROBORATE [J].