PREPARATION OF BRIDGEHEAD SUBSTITUTED BICYCLO[3.3.0]OCTANE DERIVATIVES BY THE BF3-CENTER-DOT-OET(2)-CATALYZED REARRANGEMENT OF BICYCLO[3.2.1]OCT-6-EN-8-OLS

被引:5
作者
HAYASHI, Y
USHIO, H
NARASAKA, K
机构
关键词
D O I
10.1246/cl.1994.289
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
6-t-Butyldimethylsilyl-7-methylthiobicyclo[3.2.1]oct-6-en-8-ol derivatives prepared from the [2+2] cycloadducts of 1-t-butyldimethylsilyl-2-methylthioacetylene and 2-cyclohexenones are rearranged by the treatment with BF3.OEt(2) into two types of bicycle[3.3.0]octane compounds, bicyclo[3.3.0]oct-3-en-2-one or 2-methylenebicyclo[3.3.0]oct-3-ene derivatives selectively, depending on the substituent at C-1 position.
引用
收藏
页码:289 / 292
页数:4
相关论文
共 14 条
[1]  
FOOTE CS, 1964, TETRAHEDRON, P687
[2]  
Hanson J. R., 1991, COMPREHENSIVE ORGANI, P705
[3]   MULTIPLE WAGNER-MEERWEIN SHIFT - BIOGENESIS-LIKE CONVERSION OF (+/-)-DELTA-7,8-PROTOILLUDENE TO (+/-)-HIRSUTENE AND RELATED REACTIONS [J].
HAYANO, K ;
OHFUNE, Y ;
SHIRAHAMA, H ;
MATSUMOTO, T .
HELVETICA CHIMICA ACTA, 1981, 64 (05) :1347-1364
[4]   ASYMMETRIC [2+2] CYCLOADDITION REACTION BETWEEN ALPHA,BETA-UNSATURATED ACID-DERIVATIVES AND ALKYNYL OR ALKENYL SULFIDES CATALYZED BY A CHIRAL TITANIUM REAGENT [J].
HAYASHI, Y ;
NARASAKA, K .
CHEMISTRY LETTERS, 1990, (08) :1295-1298
[5]   [2+2] CYCLOADDITION REACTION BETWEEN ALLENYL SULFIDES AND ELECTRON DEFICIENT OLEFINS PROMOTED BY LEWIS-ACIDS [J].
HAYASHI, Y ;
NIIHATA, S ;
NARASAKA, K .
CHEMISTRY LETTERS, 1990, (11) :2091-2094
[6]   ASYMMETRIC [2+2] CYCLO-ADDITION REACTION CATALYZED BY A CHIRAL TITANIUM REAGENT [J].
HAYASHI, Y ;
NARASAKA, K .
CHEMISTRY LETTERS, 1989, (05) :793-796
[7]   REACTIONS OF 1,2-PROPADIENYL SULFIDES WITH ALDEHYDES AND ACETALS CATALYZED BY BF3.OET2 [J].
NARASAKA, K ;
SHIBATA, T ;
HAYASHI, Y .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (10) :2825-2830
[8]   ASYMMETRIC [2 + 2] CYCLOADDITION REACTION CATALYZED BY A CHIRAL TITANIUM REAGENT [J].
NARASAKA, K ;
HAYASHI, Y ;
SHIMADZU, H ;
NIIHATA, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (23) :8869-8885
[9]   THE ETALCL(2)-CATALYZED CARGILL REARRANGEMENT OF BICYCLO[N.2.0] COMPOUNDS PREPARED BY THE [2+2] CYCLOADDITION OF CYCLOALKENONES AND 1-T-BUTYLDIMETHYLSILYL-2-METHYLTHIOACETYLENE [J].
NARASAKA, K ;
SHIMADZU, H ;
HAYASHI, Y .
CHEMISTRY LETTERS, 1993, (04) :621-624
[10]  
NARASAKA K, 1972, B CHEM SOC JPN, V45, P3721