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

来源：

TETRAHEDRON-ASYMMETRY | 1991年 / 2卷 / 01期

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

页码：27 / 30

页数：4

共 21 条

[1] SILYL NITRONATES IN ORGANIC-SYNTHESIS - SYNTHESIS OF 3(H-2)-FURANONES
ANDERSEN, SH
SHARMA, KK
TORSSELL, KBG
[J]. 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
ANDERSEN, SH
DAS, NB
JORGENSEN, RD
KJELDSEN, G
KNUDSEN, JS
SHARMA, SC
TORSSELL, KBG
[J]. 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
CURRAN, DP
KIM, BH
PIYASENA, HP
LONCHARICH, RJ
HOUK, KN
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (11) : 2137 - 2141
[5] CURRAN DP, 1986, SYNTHESIS-STUTTGART, P312
[6] REDUCTION OF DELTA-2-ISOXAZOLINES .3. RANEY-NICKEL CATALYZED FORMATION OF BETA-HYDROXY KETONES
CURRAN, DP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (18) : 5826 - 5833
[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
CURRAN, DP
KIM, BH
DAUGHERTY, J
HEFFNER, TA
[J]. TETRAHEDRON LETTERS, 1988, 29 (29) : 3555 - 3558
[8] REDUCTION OF SUBSTITUTED DELTA-2-ISOXAZOLINES - SYNTHESIS OF BETA-HYDROXY ACID-DERIVATIVES
CURRAN, DP
SCANGA, SA
FENK, CJ
[J]. 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
DAS, NB
TORSSELL, KBG
[J]. TETRAHEDRON, 1983, 39 (13) : 2227 - 2230

← 1 2 3 →