POWERFUL DIENOPHILES FOR ASYMMETRIC DIELS-ALDER REACTIONS - ALPHA-(2-EXO-HYDROXY-10-BORNYLSULFINYL)MALEIMIDES

被引：74

作者：

ARAI, Y

MATSUI, M

KOIZUMI, T

SHIRO, M

机构：

[1] TOYAMA MED & PHARMACEUT UNIV,FAC PHARMACEUT SCI,SUGITANI 2630,SUGITANI,TOYAMA 93001,JAPAN

[2] SHIONOGI & CO LTD,SHIONOGI RES LAB,FUKUSHIMA KU,OSAKA 553,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 06期

关键词：

D O I：

10.1021/jo00006a005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiomerically pure N-substituted alpha-(2-exo-hydroxy-10-bornylsulfinyl)maleimides 1 have been synthesized diastereoselectively, and these dienophiles undergo Diels-Alder reactions readily with furan to give the corresponding cycloadducts with high diastereoselectivity.

引用

页码：1983 / 1985

页数：3

共 38 条

[11] A SIMPLE ROUTE TO (R)-(+)-4-T-BUTOXYCYCLOPENT-2-ENONE
ESCHLER, BM
HAYNES, RK
KREMMYDAS, S
RIDLEY, DD
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (02) : 137 - 138
[12] DRAMATIC RATE ACCELERATIONS OF DIELS-ALDER REACTIONS IN 5-M LITHIUM PERCHLORATE DIETHYL-ETHER - THE CANTHARIDIN PROBLEM REEXAMINED
GRIECO, PA
NUNES, JJ
GAUL, MD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) : 4595 - 4596
[13] A MILD AND CONVENIENT METHOD FOR THE REDUCTION OF ORGANIC HALIDES BY USING A SMI2-THF SOLUTION IN THE PRESENCE OF HEXAMETHYLPHOSPHORIC TRIAMIDE (HMPA)
INANAGA, J
ISHIKAWA, M
YAMAGUCHI, M
[J]. CHEMISTRY LETTERS, 1987, (07) : 1485 - 1486
[14] REGIOSELECTIVITY AND STEREOSELECTIVITY IN UNCATALYZED AND CATALYZED DIELS-ALDER REACTIONS OF ALLENIC ESTERS WITH FURAN AND 2-METHYLFURAN
ISHAR, MPS
WALI, A
GANDHI, RP
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (08): : 2185 - 2192
[15] HIGHLY STEREOSELECTIVE TOTAL SYNTHESIS OF BETA-RIBOFURANOSYLMALONATE
KATAGIRI, N
AKATSUKA, H
HANEDA, T
KANEKO, C
SERA, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (23) : 5464 - 5470
[16] PREPARATION OF DIMETHYL 2-(PHENYLTHIO)MALEATE, DIMETHYL 2-(PHENYLTHIO)FUMARATE, AND THEIR SULFOXIDES
KAYDOS, JA
SMITH, DL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (07) : 1096 - 1099
[17] METAL HYDRIDE REDUCTIONS OF UNSYMMETRICALLY SUBSTITUTED CYCLIC ANHYDRIDES ATTACHED TO STRAINED RING-SYSTEMS
KAYSER, MM
SALVADOR, J
MORAND, P
KRISHNAMURTY, HG
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1982, 60 (10): : 1199 - 1206
[18] METAL HYDRIDE REDUCTIONS OF UNSYMMETRICAL CYCLIC ANHYDRIDES - THE IMPORTANCE OF THE ANTI-PERIPLANAR EFFECT ON THE REGIOSELECTIVITY OF THESE REACTIONS
KAYSER, MM
WIPFF, G
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1982, 60 (10): : 1192 - 1198
[19] HIGHLY DIASTEREOSELECTIVE DIELS-ALDER REACTION OF OPTICALLY-ACTIVE ETHYL 2-PARA-TOLYLSULFINYLMETHYLENEPROPIONATE WITH CYCLOPENTADIENE
KOIZUMI, T
HAKAMADA, I
YOSHII, E
[J]. TETRAHEDRON LETTERS, 1984, 25 (01) : 87 - 90
[20] KOIZUMI T, 1988, TETRAHEDRON LETT, V29, P3689

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