STEREOSELECTIVE SYNTHESIS OF CIS-DECALINS VIA DIELS-ALDER AND DOUBLE MICHAEL ADDITION OF SUBSTITUTED NAZAROV REAGENTS

被引:56
作者
LAVALLEE, JF [1 ]
SPINO, C [1 ]
RUEL, R [1 ]
HOGAN, KT [1 ]
DESLONGCHAMPS, P [1 ]
机构
[1] UNIV SHERBROOKE,FAC SCI,DEPT CHIM,SYNTHESE ORGAN LAB,SHERBROOKE J1K 2R1,QUEBEC,CANADA
来源
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1992年 / 70卷 / 05期
关键词
D O I
10.1139/v92-179
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The base-catalyzed cycloaddition and double Michael cyclization of substituted Nazarov reagents an of 1-phenylsulfinyl analogs, with 2-carbomethoxy-2-cyclohexen-1-one 1 yielding cis-decalins is reported. The reaction is highly stereoselective affording cis,cis- or cis,trans-decalins. Mechanistic aspects are briefly discussed.
引用
收藏
页码:1406 / 1426
页数:21
相关论文
共 39 条
[1]   INTRAMOLECULAR MICHAEL ADDITION OF CYCLIC BETA-KETOESTER ON CONJUGATED OLEFINIC KETONE, A STEREOELECTRONICALLY CONTROLLED PROCESS [J].
BERTHIAUME, G ;
LAVALLEE, JF ;
DESLONGCHAMPS, P .
TETRAHEDRON LETTERS, 1986, 27 (45) :5451-5454
[2]   A NEW EFFICIENT SYNTHESIS OF SUBSTITUTED NAZAROV REAGENTS - A WITTIG-HORNER-EMMONS APPROACH [J].
BODALSKI, R ;
PIETRUSIEWICZ, KM ;
MONKIEWICZ, J ;
KOSZUK, J .
TETRAHEDRON LETTERS, 1980, 21 (23) :2287-2290
[3]   STEREOCONTROL IN THE INTRAMOLECULAR DIELS-ALDER REACTION .5. PREPARATION OF A TETRACYCLIC INTERMEDIATE FOR IKARUGAMYCIN [J].
BOECKMAN, RK ;
NAPIER, JJ ;
THOMAS, EW ;
SATO, RI .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4152-4154
[4]   C-ACYLATION UNDER VIRTUALLY NEUTRAL CONDITIONS [J].
BROOKS, DW ;
LU, LDL ;
MASAMUNE, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (01) :72-74
[5]   DIELS-ALDER REACTIONS OF 2-CARBOMETHOXY-4,4-DIMETHYLCYCLOPENTENONE [J].
CAINE, D ;
HARRISON, CR ;
VANDERVEER, DG .
TETRAHEDRON LETTERS, 1983, 24 (13) :1353-1356
[6]   1ST STEREOSPECIFIC SYNTHESIS OF E-GAMMA-BISABOLENE - A METHOD FOR THE CONCURRENT GENERATION OF A RING AND A TETRASUBSTITUTED EXOCYCLIC DOUBLE-BOND [J].
COREY, EJ ;
SEIBEL, WL .
TETRAHEDRON LETTERS, 1986, 27 (08) :905-908
[7]  
DESLONGCHAMPS P, 1983, ORGANIC CHEM SERIES, V1, P275
[8]   [3,3]SIGMATROPIC REARRANGEMENTS OF 1,5-DIENE ALKOXIDES - POWERFUL ACCELERATING EFFECTS OF ALKOXIDE SUBSTITUENT [J].
EVANS, DA ;
GOLOB, AM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (16) :4765-4766
[9]  
GOLDMANN S, 1980, SYNTHESIS-STUTTGART, P640
[10]  
Ho, 1988, CARBOCYCLE CONSTRUCT