ENDO SELECTIVE CYCLIZATIONS OF SELENONIUM ION INTERMEDIATE - EFFICIENT FORMATION OF 1-HALO-3-SELENO-CYCLOHEXANES

被引:13
作者
KATAOKA, T [1 ]
YOSHIMATSU, M [1 ]
SHIMIZU, H [1 ]
HORI, M [1 ]
机构
[1] GIFU PHARMACEUT UNIV,6-1 MITAHORA HIGASHI 5 CHOME,GIFU 502,JAPAN
关键词
D O I
10.1016/S0040-4039(00)71230-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Selenoacetal 1 was cyclized with tin(IV) chloride in the 6-Endo-Trig mode to give 1-chloro-3-methylselenocyclohexanes (2a,b) regio- and stereoselectively. Bromo- or iodocyclohexane derivatives were afforded by use of tin(IV) bromide or titanium(IV) iodide, respectively.
引用
收藏
页码:105 / 108
页数:4
相关论文
共 14 条
[1]   VINYLSILANE-TERMINATED AND ALKYNYLSILANE-TERMINATED CYCLIZATION REACTIONS [J].
BLUMENKOPF, TA ;
OVERMAN, LE .
CHEMICAL REVIEWS, 1986, 86 (05) :857-873
[2]   VINYLLITHIUM CYCLIZATIONS WITH UNACTIVATED ALKENES AS INTERNAL ELECTROPHILES - STEREOSELECTIVE FORMATION OF SUBSTITUTED METHYLENECYCLOPENTANES [J].
CHAMBERLIN, AR ;
BLOOM, SH ;
CERVINI, LA ;
FOTSCH, CH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (14) :4788-4796
[3]   CONVERSION OF ALDEHYDES AND KETONES INTO SELENOACETALS - USE OF TRIS-(PHENYLSELENO)BORANE AND TRIS-(METHYLSELENO)BORANE [J].
CLIVE, DLJ ;
MENCHEN, SM .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (24) :4279-4285
[4]   SYNTHESIS OF OPTICALLY-ACTIVE (-)-TRACHELANTHAMIDINE FROM L-PROLINOL [J].
ISHIBASHI, H ;
OZEKI, H ;
IKEDA, M .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (09) :654-655
[5]  
KATAOKA T, 1990, HETEROCYCLES, V31, P889
[6]   VINYL RADICAL GENERATION WITH SELENOBORANE AND ITS APPLICATION TO CYCLIZATION REACTION OF ENYNES [J].
KATAOKA, T ;
YOSHIMATSU, M ;
SHIMIZU, H ;
HORI, M .
TETRAHEDRON LETTERS, 1990, 31 (41) :5927-5930
[7]   CHEMISTRY OF O-SILYLATED KETENE ACETALS - AN EFFICIENT SYNTHESIS OF ALPHA-THIO-N-HETEROCYCLES FROM OMEGA-AMIDOSULFOXIDES BY A NOVEL INTRAMOLECULAR PUMMERER-TYPE REARRANGEMENT [J].
KITA, Y ;
TAMURA, O ;
MIKI, T ;
TAMURA, Y .
TETRAHEDRON LETTERS, 1987, 28 (51) :6479-6480
[8]   SYNTHESIS OF ALPHA-SELENOALKYLLITHIUM COMPOUNDS [J].
KRIEF, A ;
DUMONT, W ;
CLAREMBEAU, M ;
BERNARD, G ;
BADAOUI, E .
TETRAHEDRON, 1989, 45 (07) :2005-2022
[9]   SYNTHESIS OF A NEW TETRACYCLIC SYSTEM RELATED TO APTAZAPINE (CGS-7525A) BY ONE-POT DOUBLE ANNELATION [J].
MASSA, S ;
MAI, A ;
CORELLI, F .
TETRAHEDRON LETTERS, 1988, 29 (49) :6471-6474
[10]   SELENIUM STABILIZED CARBENIUM IONS - LEWIS ACID MEDIATED SELENO ALKYLATION OF KETONES [J].
NSUNDA, KM ;
HEVESI, L .
TETRAHEDRON LETTERS, 1984, 25 (39) :4441-4444