Intramolecular cycloaddition of nitrones with sulfur-substituted dienes and its synthetic applications

被引:10
作者
Chou, SSP
Yu, YJ
机构
[1] Department of Chemistry, Fu Jen Catholic University
关键词
D O I
10.1016/S0040-4039(97)01037-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of sulfur-substituted dienyl nitrones were conviently prepared from the 3-sulfolene precursors. Intramolecular 1,3-dipolar cycloaddition reactions gave the fused bicyclic isoxazolidines. The regio- and stereochemical outcome of these reactions as well as the synthetic applications have been explored. (C) 1997 Elsevier Science Ltd.
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收藏
页码:4803 / 4806
页数:4
相关论文
共 22 条
[1]   INTRAMOLECULAR CYCLOADDITION OF NITRONES [J].
AURICH, HG ;
BOUTAHAR, M ;
KOSTER, H ;
MOBUS, KD ;
RUIZ, L .
CHEMISCHE BERICHTE, 1990, 123 (10) :1999-2014
[2]   REGIOCHEMISTRY IN THE INTRAMOLECULAR CYCLO-ADDITIONS OF SUBSTITUTED 5-ALKENYL AND 6-ALKENYL NITRONES [J].
BALDWIN, SW ;
WILSON, JD ;
AUBE, J .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (23) :4432-4439
[3]  
BARAN J, 1987, J AM CHEM SOC, V105, P6519
[4]   INTRAMOLECULAR DIELS-ALDER REACTIONS VIA SULFONE-SUBSTITUTED 3-SULFOLENES [J].
CHOU, SSP ;
LEE, CS ;
CHENG, MC ;
TAI, HP .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (08) :2010-2013
[5]   SYNTHESIS AND CYCLIZATION OF SULFUR-SUBSTITUTED AZIDO DIENES TO PYRROLIZIDINE AND INDOLIZIDINE MOIETIES [J].
CHOU, SSP ;
TSAO, HJ ;
LEE, CM ;
SUN, CM .
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1993, 40 (01) :53-57
[6]   REGIOCONTROLLED AND STEREOCONTROLLED SYNTHESIS AND DIELS-ALDER REACTIONS OF (Z)-2-(PHENYLTHIO)-1-(TRIMETHYLSILYL)-1,3-BUTADIENE [J].
CHOU, SSP ;
CHAO, MH .
TETRAHEDRON LETTERS, 1995, 36 (48) :8825-8828
[7]   INTRAMOLECULAR DIELS-ALDER REACTIONS OF SULFUR-SUBSTITUTED DIENES VIA 3-SULFOLENES [J].
CHOU, SSP ;
WEY, SJ .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (04) :1270-1274
[8]   STEREOSPECIFIC SYNTHESIS OF RACEMIC DAUNOSAMINE - DIASTEREOFACIAL SELECTIVITY IN A NITRONE CYCLOADDITION [J].
DESHONG, P ;
LEGINUS, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (06) :1686-1688
[9]   MULTIPLY CONVERGENT SYNTHESES VIA CONJUGATE-ADDITION REACTIONS TO CYCLOALKENYL SULFONES [J].
FUCHS, PL ;
BRAISH, TF .
CHEMICAL REVIEWS, 1986, 86 (05) :903-917
[10]   THE NITRONE ROUTE TO LINEARLY FUSED TRICYCLOPENTANOIDS - ANOTHER SYNTHESIS OF HIRSUTENE [J].
FUNK, RL ;
BOLTON, GL .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (25) :5021-5022