ASYMMETRIC INDUCTION IN SILYL NITRONATE CYCLOADDITIONS TO OPPOLZER CHIRAL SULTAM DERIVATIVES

被引:37
作者
KIM, BH
LEE, JY
KIM, KM
WHANG, DM
机构
[1] Department of Chemistry, Pohang Institute of Science and Technology, Pohang, 790-600
关键词
D O I
10.1016/S0957-4166(00)82151-5
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Silyl nitronate cycloadditions to Oppolzer's chiral sultam derivatives, followed by the elimination of the sily alcohols from the resulting N-silyloxyisoxazolidines, provide DELTA-2-isoxazolines in good stereoselectivity (ca. 89/11). The favored transition state is suggested in the light of the X-ray crystal structure of a major cycloadduct.
引用
收藏
页码:27 / 30
页数:4
相关论文
共 21 条
[1]   SILYL NITRONATES IN ORGANIC-SYNTHESIS - SYNTHESIS OF 3(H-2)-FURANONES [J].
ANDERSEN, SH ;
SHARMA, KK ;
TORSSELL, KBG .
TETRAHEDRON, 1983, 39 (13) :2241-2245
[2]   SILYL NITRONATES IN ORGANIC-SYNTHESIS - ROUTES TO HETEROCYCLES AND CYCLOPENTANOIDS - SYNTHESIS OF ALLETHROLONE AND CALYTHRONE - ACYLATION AND CYANOHYDROXYLATION OF DOUBLE-BONDS - AN EXPLORATORY-STUDY [J].
ANDERSEN, SH ;
DAS, NB ;
JORGENSEN, RD ;
KJELDSEN, G ;
KNUDSEN, JS ;
SHARMA, SC ;
TORSSELL, KBG .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1982, 36 (01) :1-14
[3]  
BREUER E, 1989, NITRONES NITRONATES, P297
[4]   ASYMMETRIC INDUCTION IN NITRILE OXIDE CYCLOADDITIONS TO OPTICALLY-ACTIVE ACRYLATES - COMPARISONS OF ACRYLATE CONFORMATIONS IN THERMAL AND ACID-CATALYZED 1,3-DIPOLAR AND DIELS-ALDER CYCLOADDITION TRANSITION-STATES [J].
CURRAN, DP ;
KIM, BH ;
PIYASENA, HP ;
LONCHARICH, RJ ;
HOUK, KN .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (11) :2137-2141
[5]  
CURRAN DP, 1986, SYNTHESIS-STUTTGART, P312
[7]   THE PREPARATION OF OPTICALLY-ACTIVE DELTA-2-ISOXAZOLINES - A MODEL FOR ASYMMETRIC INDUCTION IN THE NON LEWIS ACID-CATALYZED REACTIONS OF OPPOLZERS CHIRAL SULTAM [J].
CURRAN, DP ;
KIM, BH ;
DAUGHERTY, J ;
HEFFNER, TA .
TETRAHEDRON LETTERS, 1988, 29 (29) :3555-3558
[8]   REDUCTION OF SUBSTITUTED DELTA-2-ISOXAZOLINES - SYNTHESIS OF BETA-HYDROXY ACID-DERIVATIVES [J].
CURRAN, DP ;
SCANGA, SA ;
FENK, CJ .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (19) :3474-3478
[9]  
CURRAN DP, 1990, ORGCHEM, V55, P4585
[10]   SILYL NITRONATES IN ORGANIC-SYNTHESIS - SYNTHESIS OF PROSTAGLANDIN INTERMEDIATES [J].
DAS, NB ;
TORSSELL, KBG .
TETRAHEDRON, 1983, 39 (13) :2227-2230