ASYMMETRIC-SYNTHESIS OF CIS-HYDRINDANEDIONES BY DIELS-ALDER REACTION OF CYCLOPENTENONES BEARING A 3-SULFONYL-1,3-OXAZOLIDINE RING AS CHIRAL AUXILIARY-INFINITY

被引：15

作者：

HOFFMANN, H

BOLTE, M

BERGER, B

HOPPE, D

机构：

[1] CHRISTIAN ALBRECHTS UNIV KIEL,INST ORGAN CHEM,OLSHAUSENSTR 40,D-24118 KIEL,GERMANY

[2] UNIV FRANKFURT,INST ORGAN CHEM,D-60439 FRANKFURT,GERMANY

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 41期

关键词：

ASYMMETRIC DIELS-ALDER REACTION; CHIRAL; 2-CYCLOPENTENONES; CHIRAL 1,3-OXAZOLIDINES;

D O I：

10.1016/0040-4039(93)88098-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Diels-Alder reaction of enantiomerically pure 2- and 5-(1,3-oxazolidin-2-yl)-2-cyclopentenones 8 or 14 and 2-(trimethylsilyloxy)-1,3-butadiene 9 under Lewis-acid catalysis yields (after hydrolysis) protected 3,7-dioxohydrindane-carbaldehydes 11 or 16, respectively.

引用

收藏

页码：6537 / 6540

页数：4

相关论文

共 21 条

[1]

AGNELLI EC, 1982, J ORG CHEM, V47, P5056

[2] 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

[3] SECONDARY ORBITAL INTERACTIONS DETERMINING REGIOSELECTIVITY IN DIELS-ALDER REACTION [J].

ALSTON, PV ;

OTTENBRI.RM ;

SHILLADY, DD .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (23) :4075-4077

[4] NOREPHEDRINE DERIVED 2-METHOXY OXAZOLIDINES AS CHIRAL FORMYL CATION EQUIVALENTS [J].

BERNARDI, A ;

CARDANI, S ;

CARUGO, O ;

COLOMBO, L ;

SCOLASTICO, C ;

VILLA, R .

TETRAHEDRON LETTERS, 1990, 31 (19) :2779-2782

[5] NOREPHEDRINE DERIVED OXAZOLIDINES AS CHIRAL ACYLATING AGENTS - AN NMR-STUDY OF THE INTERMEDIATE CATIONS [J].

BERNARDI, A ;

CARDANI, S ;

POLI, G ;

POTENZA, D ;

SCOLASTICO, C .

TETRAHEDRON, 1992, 48 (07) :1343-1352

[6] NORPSEUDOEPHEDRINE-DERIVED 2-METHOXY-3-SULFONYL-1,3-OXAZOLIDINES - CHIRAL, HIGHLY DIASTEREOSELECTIVE FORMYL CATION EQUIVALENTS [J].

CONDEFRIEBOES, K ;

HOPPE, D .

TETRAHEDRON, 1992, 48 (29) :6011-6020

[7]

CONDEFRIEBOES K, 1990, SYNLETT, P99

[8] TOTAL SYNTHESIS OF DIHYDROCOSTUNOLIDE [J].

COREY, EJ ;

HORTMANN, AG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (24) :5736-&

[9] NEW ASYMMETRIC DIELS-ALDER CYCLOADDITION REACTIONS - CHIRAL ALPHA,BETA-UNSATURATED CARBOXIMIDES AS PRACTICAL CHIRAL ACRYLATE AND CROTONATE DIENOPHILE SYNTHONS [J].

EVANS, DA ;

CHAPMAN, KT ;

BISAHA, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (15) :4261-4263

[10] ENANTIOSELECTIVE CONSTRUCTION OF HIGHLY FUNCTIONALIZED BICYCLO[4.3.0] SYSTEM THROUGH DIELS-ALDER CYCLOADDITION [J].

FUJI, K ;

TANAKA, K ;

ABE, H ;

ITOH, A ;

NODE, M ;

TAGA, T ;

MIWA, Y ;

SHIRO, M .

TETRAHEDRON-ASYMMETRY, 1991, 2 (12) :1319-1327