POLYMER-SUPPORTED CHIRAL LEWIS-ACIDS AS ASYMMETRIC CATALYSTS FOR DIELS-ALDER REACTIONS OF METHACROLEIN WITH CYCLOPENTADIENE

被引:44
作者
ITSUNO, S
KAMAHORI, K
WATANABE, K
KOIZUMI, T
ITO, K
机构
[1] Department of Materials Science, Toyohashi University of Technology, Toyohashi, 441, Tempaku-cho
关键词
D O I
10.1016/0957-4166(94)80008-1
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Insoluble polymer-supported chiral Lewis acids were prepared from monobromoborane or borane with crosslinked polymers having a chiral moiety such as an amino alcohol, diol, or N-sulfonylamino acid. These polymers were used as chiral catalysts for Diels-Alder reactions of methacrolein with cyclopentadiene to give optically active cycloadduct.
引用
收藏
页码:523 / 526
页数:4
相关论文
共 24 条
[1]   VAULTED BIARYLS AS CHIRAL LIGANDS FOR ASYMMETRIC CATALYTIC DIELS-ALDER REACTIONS [J].
BAO, JM ;
WULFF, WD ;
RHEINGOLD, AL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (09) :3814-3815
[2]   ASYMMETRIC DIELS-ALDER REACTIONS OF CYCLOPENTADIENE WITH N-CROTONOYL AND N-ACRYLOYL-4,4-DIMETHYL-1,3-OXAZOLIDIN-2-ONE, MEDIATED BY CHIRAL LEWIS-ACIDS [J].
CHAPUIS, C ;
JURCZAK, J .
HELVETICA CHIMICA ACTA, 1987, 70 (02) :436-440
[3]   1ST APPLICATION OF ATTRACTIVE INTRAMOLECULAR INTERACTIONS TO THE DESIGN OF CHIRAL CATALYSTS FOR HIGHLY ENANTIOSELECTIVE DIELS-ALDER REACTIONS [J].
COREY, EJ ;
LOH, TP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (23) :8966-8967
[4]   PRACTICAL ENANTIOSELECTIVE DIELS-ALDER AND ALDOL REACTIONS USING A NEW CHIRAL CONTROLLER SYSTEM [J].
COREY, EJ ;
IMWINKELRIED, R ;
PIKUL, S ;
XIANG, YB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) :5493-5495
[5]   THE ORIGIN OF GREATER THAN 200/1 ENANTIOSELECTIVITY IN A CATALYTIC DIELS-ALDER REACTION AS REVEALED BY PHYSICAL AND CHEMICAL STUDIES [J].
COREY, EJ ;
LOH, TP ;
ROPER, TD ;
AZIMIOARA, MD ;
NOE, MC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (21) :8290-8292
[6]   ASYMMETRIC DIELS-ALDER REACTIONS OF CARBOXYLIC ESTER DIENOPHILES PROMOTED BY CHIRAL LEWIS-ACIDS [J].
DEVINE, PN ;
OH, T .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (01) :396-399
[7]   CHIRAL (ACYLOXY)BORANE (CAB) - A POWERFUL AND PRACTICAL CATALYST FOR ASYMMETRIC DIELS-ALDER REACTIONS [J].
FURUTA, K ;
SHIMIZU, S ;
MIWA, Y ;
YAMAMOTO, H .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) :1481-1483
[8]   ACYLOXYBORANE - AN ACTIVATING DEVICE FOR CARBOXYLIC-ACIDS [J].
FURUTA, K ;
MIWA, Y ;
IWANAGA, K ;
YAMAMOTO, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (18) :6254-6255
[9]   ASYMMETRIC DIELS-ALDER REACTION CATALYZED BY CHIRAL ALKOXYALUMINIUM DICHLORIDE [J].
HASHIMOTO, S ;
KOMESHIMA, N ;
KOGA, K .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (10) :437-438