CATALYTIC METHYLALUMINUM DICHLORIDE - AN EFFICIENT METHOD FOR ACCELERATING THE INTRAMOLECULAR DIELS-ALDER REACTION OF THE FURAN DIENE

被引:36
作者
ROGERS, C [1 ]
KEAY, BA [1 ]
机构
[1] UNIV CALGARY,CALGARY T2N 1N4,ALBERTA,CANADA
关键词
INTRAMOLECULAR DIELS-ALDER REACTION; FURAN; METHYLALUMINUM DICHLORIDE; CATALYST;
D O I
10.1016/0040-4039(91)80197-E
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Catalytic (10 mol%) methylaluminum dichloride was found to be an efficient catalyst for the intramolecular Diels-Alder reaction of the furan diene providing oxatricyclo adducts at -65-degrees-C within two hours in yields ranging from good to excellent.
引用
收藏
页码:6477 / 6480
页数:4
相关论文
共 25 条
[1]  
Ciganek E., 1984, ORG REACT NY, V32, P1, DOI DOI 10.1002/0471264180.OR032.01
[2]   STEREOCHEMICAL ASPECTS OF THE INTRAMOLECULAR DIELS-ALDER REACTION [J].
CRAIG, D .
CHEMICAL SOCIETY REVIEWS, 1987, 16 (02) :187-238
[3]   INTRA-MOLECULAR DIELS-ALDER FURAN APPROACH IN SYNTHESIS - 11-OXATRICYCLO [6.2.1.01,6] UNDEC-9-EN-5-ONE [J].
DECLERCQ, PJ ;
VANROYEN, LA .
SYNTHETIC COMMUNICATIONS, 1979, 9 (09) :771-780
[4]   THE INTRAMOLECULAR DIELS-ALDER REACTION - RECENT ADVANCES AND SYNTHETIC APPLICATIONS [J].
FALLIS, AG .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (02) :183-234
[5]   STEREOSELECTIVE SYNTHESIS OF DECALINS VIA TANDEM PHOTOOXIDATION - INTRAMOLECULAR DIELS-ALDER REACTIONS OF BIS-FURANS [J].
FERINGA, BL ;
GELLING, OJ ;
MEESTERS, L .
TETRAHEDRON LETTERS, 1990, 31 (49) :7201-7204
[6]   THE HIGH-PRESSURE MEDIATED INTRAMOLECULAR DIELS-ALDER REACTION OF FURANS - FACTORS CONTROLLING CYCLO-ADDITION WITH MONOACTIVATED DIENOPHILES [J].
HARWOOD, LM ;
LEEMING, SA ;
ISAACS, NS ;
JONES, G ;
PICKARD, J ;
THOMAS, RM ;
WATKIN, D .
TETRAHEDRON LETTERS, 1988, 29 (39) :5017-5020
[8]   THERMAL AND CATALYZED INTRAMOLECULAR DIELS-ALDER CYCLIZATIONS OF 2,8,10-UNDECATRIENALS [J].
MARSHALL, JA ;
SHEARER, BG ;
CROOKS, SL .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (07) :1236-1245
[9]   ACYCLIC STEREOCONTROL IN CATALYZED INTRAMOLECULAR DIELS-ALDER CYCLIZATIONS LEADING TO OCTAHYDRONAPHTHALENECARBOXALDEHYDES [J].
MARSHALL, JA ;
GROTE, J ;
AUDIA, JE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (04) :1186-1194
[10]   DIELS-ALDER CYCLIZATION OF 2,8,10-UNDECATRIENALS AS A ROUTE TO 1,2,3,4,4A,5,6,8A-OCTAHYDRONAPHTHALENES [J].
MARSHALL, JA ;
AUDIA, JE ;
GROTE, J ;
SHEARER, BG .
TETRAHEDRON, 1986, 42 (11) :2893-2902