Cobalt-mediated cycloisomerization of δ-substituted ε-acetylenic β-ketoesters construction of angular triquinane by a sequence ene/Pauson-Khand reactions

被引:54
作者
Renaud, JL [1 ]
Aubert, C [1 ]
Malacria, M [1 ]
机构
[1] Univ Paris 06, CNRS, Lab Chim Organ Synth, F-75252 Paris 05, France
关键词
cobalt and compounds; ene reaction; 1,4 diastereoselection; Pauson-Khand reaction;
D O I
10.1016/S0040-4020(99)00172-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The preparation of delta-substituted epsilon-acetylenic beta-ketoesters is fully described. Their cobalt-mediated Conia-ene reactions led to variously functionalized methylenecyclopentanes in high yields and with a moderate control of the 1,4 diastereoselectivity. A sequence involving the cobalt-mediated ene and Pauson-Khand reactions is presented and allowed the construction of the angular triquinane framework. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5113 / 5128
页数:16
相关论文
共 29 条
[1]   EFFICIENT SYNTHESIS OF TERMINAL BIS(TRIMETHYLSILYL)-ALPHA,OMEGA-DIYNES [J].
AUDERSET, PC ;
DREIDING, AS ;
GESING, ERF .
SYNTHETIC COMMUNICATIONS, 1983, 13 (11) :881-887
[2]  
COREY EJ, 1972, TETRAHEDRON LETT, P3769
[3]  
COREY EJ, 1973, TETRAHEDRON LETT, P1495
[4]   New cobalt-catalyzed cycloisomerization of epsilon-acetylenic beta-keto esters. Application to a powerful cyclization reactions cascade [J].
Cruciani, P ;
Stammler, R ;
Aubert, C ;
Malacria, M .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (08) :2699-2708
[5]   STUDIES ON DIASTEREOSELECTIVITY OF THE COBALT(I) CATALYZED CYCLOISOMERIZATION OF SUBSTITUTED EPSILON-ACETYLENIC BETA-KETOESTER [J].
CRUCIANI, P ;
AUBERT, C ;
MALACRIA, M .
TETRAHEDRON LETTERS, 1994, 35 (36) :6677-6680
[6]   A NEW CYCLIZATION REACTIONS CASCADE-ENE TYPE, [2+2+2], [4+2] - STEREOSELECTIVE FORMATION OF 6 CARBON-CARBON BONDS AND 4 RINGS IN A ONE-POT SEQUENCE [J].
CRUCIANI, P ;
AUBERT, C ;
MALACRIA, M .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (09) :2664-2665
[7]  
HOMMES H, 1980, RECL TRAV CHIM PAY B, V99, P113
[8]  
JEONG N, 1991, SYNLETT, P204
[9]  
Jones T. K., 1986, ORG SYNTH, V64, P182
[10]   ORGANOCOBALT COMPLEXES .2. REACTION OF ACETYLENEHEXACARBONYLDICOBALT COMPLEXES, (R1C2R2)CO2(CO)6, WITH NORBORNENE AND ITS DERIVATIVES [J].
KHAND, IU ;
KNOX, GR ;
PAUSON, PL ;
WATTS, WE ;
FOREMAN, MI .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (09) :977-981