AN EFFICIENT PREPARATION OF 3-AZABICYCLO[3.3.0]OCT-5-EN-7-ONES FROM PROPARGYL ALCOHOL-COBALT COMPLEXES VIA NICHOLAS REACTION WITH AMIDIC NITROGEN NUCLEOPHILES FOLLOWED BY PAUSON-KHAND CYCLIZATION

被引:46
作者
JEONG, N [1 ]
YOO, SE [1 ]
LEE, SJ [1 ]
LEE, SH [1 ]
CHUNG, YK [1 ]
机构
[1] SEOUL NATL UNIV,DEPT CHEM,SEOUL 151,SOUTH KOREA
关键词
D O I
10.1016/S0040-4039(00)71257-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
3-Azabicyclo [3.3.0]-oct-5-en-7-ones were efficiently prepared from cobalt-propagyl alcohol complexes and various allyl amides via Nicholas reaction in the presence of BF3Et2O followed by Pauson-Khand cyclization promoted with trimethylamine N-oxide or SiO2.
引用
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页码:2137 / 2140
页数:4
相关论文
共 27 条
[1]   A SIMPLE ORGANOCOBALT MEDIATED SYNTHESIS OF SUBSTITUTED 3-OXABICYCLO[3.3.0]OCT-6-EN-7-ONES [J].
BILLINGTON, DC ;
WILLISON, D .
TETRAHEDRON LETTERS, 1984, 25 (36) :4041-4044
[2]   THE SYNTHESIS OF NITROGEN-HETEROCYCLES VIA THE INTRAMOLECULAR KHAND REACTION - FORMATION OF TETRA-HYDROCYCLOPENTA[C]PYRROL-5(1H)-ONES AND HEXA-HYDROCYCLOPENTA[C]PYRROL-5(1H)-ONES AND HEXAHYDRO-6H-2-PYRINDIN-6-ONES [J].
BROWN, SW ;
PAUSON, PL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (04) :1205-1209
[3]   GENERAL-SYNTHESIS OF OMEGA-ACETYLENIC VINYL ESTERS AND ETHERS [J].
CROUDACE, MC ;
SCHORE, NE .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (26) :5357-5363
[4]   STEREOSELECTIVITY OF INTRAMOLECULAR DICOBALT OCTACARBONYL ALKENE ALKYNE CYCLIZATIONS - SHORT SYNTHESIS OF DL-CORIOLIN [J].
EXON, C ;
MAGNUS, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (08) :2477-2478
[5]   A NOVEL AND EFFICIENT SYNTHESIS OF L-VINYLGLYCINE [J].
HANESSIAN, S ;
SAHOO, SP .
TETRAHEDRON LETTERS, 1984, 25 (14) :1425-1428
[6]  
JEONG N, 1991, IN PRESS SYNLETT
[7]  
KHAND IU, 1973, J CHEM SOC P1, P97
[8]   SYNTHESIS OF THE ANGULARLY FUSED TRIQUINANE SKELETON VIA INTRAMOLECULAR ORGANOMETALLIC CYCLIZATION [J].
KNUDSEN, MJ ;
SCHORE, NE .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (25) :5025-5026
[9]   STEREOSPECIFIC DICOBALT OCTACARBONYL MEDIATED ENYNE CYCLIZATION FOR THE SYNTHESIS OF THE CYTOTOXIC SESQUITERPENE (+/-)-QUADRONE [J].
MAGNUS, P ;
PRINCIPE, LM ;
SLATER, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (08) :1483-1486
[10]   DICOBALTOCTACARBONYL ALKYNE COMPLEXES AS INTERMEDIATES IN THE SYNTHESIS OF BICYCLO[3.3.0]OCTENONES FOR THE SYNTHESIS OF CORIOLIN AND HIRSUTIC ACID [J].
MAGNUS, P ;
EXON, C ;
ALBAUGHROBERTSON, P .
TETRAHEDRON, 1985, 41 (24) :5861-5869