O-BRIDGED MEDIUM-SIZED RINGS VIA BICYCLIC OXONIUM YLIDES

被引:58
作者
WEST, FG [1 ]
EBERLEIN, TH [1 ]
TESTER, RW [1 ]
机构
[1] PENN STATE UNIV,DEPT CHEM,SCHUYLKILL HAVEN,PA 17972
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 23期
关键词
D O I
10.1039/p19930002857
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Fused bicyclic oxonium ylides, generated with catalytic Rh2(OAc)4 from cyclic ethers bearing pendant diazo ketones, undergo a [1,2]- or [2,3]-shift to give O-bridged seven- or eight-membered carbocycles, in several cases with a high degree of stereoselectivity.
引用
收藏
页码:2857 / 2859
页数:3
相关论文
共 31 条
[1]   RHODIUM (II) CATALYZED-REACTIONS OF DIAZO-CARBONYL COMPOUNDS [J].
ADAMS, J ;
SPERO, DM .
TETRAHEDRON, 1991, 47 (10-11) :1765-1808
[2]   RHODIUM ACETATE CATALYZES THE ADDITION OF CARBENOIDS ALPHA-OXYGENS TO ETHER OXYGENS [J].
ADAMS, J ;
POUPART, MA ;
GRENIER, L ;
SCHALLER, C ;
OUIMET, N ;
FRENETTE, R .
TETRAHEDRON LETTERS, 1989, 30 (14) :1749-1752
[3]  
ADAMS J, 1987, TETRAHEDRON LETT, P4773
[4]   YLIDE FORMATION AND REARRANGEMENT IN REACTION OF CARBENE WITH DIVALENT SULFUR-COMPOUNDS [J].
ANDO, W .
ACCOUNTS OF CHEMICAL RESEARCH, 1977, 10 (05) :179-185
[5]   HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS [J].
BLANCHETTE, MA ;
CHOY, W ;
DAVIS, JT ;
ESSENFELD, AP ;
MASAMUNE, S ;
ROUSH, WR ;
SAKAI, T .
TETRAHEDRON LETTERS, 1984, 25 (21) :2183-2186
[6]   SYNTHESIS OF CYCLIC ETHERS FROM COPPER CARBENOIDS BY FORMATION AND REARRANGEMENT OF OXONIUM YLIDES [J].
CLARK, JS ;
KROWIAK, SA ;
STREET, LJ .
TETRAHEDRON LETTERS, 1993, 34 (27) :4385-4388
[7]  
DAVIES HML, 1991, COMPREHENSIVE ORGANI, V4
[8]   CATALYTIC METHODS FOR METAL CARBENE TRANSFORMATIONS [J].
DOYLE, MP .
CHEMICAL REVIEWS, 1986, 86 (05) :919-939
[9]   THE STEVENS [1,2]-SHIFT OF OXONIUM YLIDES - A ROUTE TO SUBSTITUTED TETRAHYDROFURANONES [J].
EBERLEIN, TH ;
WEST, FG ;
TESTER, RW .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (12) :3479-3482
[10]  
GILLESPIE RJ, 1979, J CHEM SOC CHEM COMM, V50