A SIMPLE, EFFICIENT, 2-STEP SYNTHESIS OF SYMMETRICAL 2,7-DIALKYL-1,6-DIOXASPIRO[4.4]NONANES

被引:12
作者
BALLINI, R
BOSICA, G
USELLI, A
机构
[1] Dipartimento di Scienze Chimiche, università Camerino
关键词
D O I
10.1002/jhet.5570310145
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A two-step synthesis of symmetric 2,7-dialkyl-1,6-dioxaspiro[4.4]nonanes has been achieved by double Michael addition of nitromethane with two moles of enones on Amberlyst A21, followed by in situ reduction with sodium borohydride, then spontaneous spiroketalization of the obtained nitrodiol, by the Nef reaction under acidic conditions, affords the title compounds in good yields.
引用
收藏
页码:259 / 260
页数:2
相关论文
共 12 条
[1]   HYDROXY-FUNCTIONALIZED CONJUGATED NITROOLEFINS AS IMMEDIATE PRECURSORS OF SPIROKETALS - A NEW SYNTHESIS OF 1,7-DIOXASPIRO[5.5]UNDECANE AND (E)-2-METHYL-1,7-DIOXASPIRO[5.6]DODECANE [J].
BALLINI, R ;
PETRINI, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (23) :3159-3160
[2]  
BERGSTROM G, 1982, Z NATURFORSCH C, V37, P1124
[4]  
ENDERS D, 1990, SYNTHESIS-STUTTGART, P1013
[5]   SPIROKETALS IN THE MANDIBULAR GLANDS OF ANDRENA BEES [J].
FRANCKE, W ;
REITH, W ;
BERGSTROM, G ;
TENGO, J .
NATURWISSENSCHAFTEN, 1980, 67 (03) :149-150
[6]  
FRANCKE W, 1979, LIEBIGS ANN CHEM, P1
[7]  
FRANCKE W, 1981, Z NATURFORSCH C, V36, P928
[8]  
KLUGE AF, 1986, HETEROCYCLES, V24, P1699
[9]   SYNTHESIS OF OPTICALLY-ACTIVE PHEROMONES [J].
MORI, K .
TETRAHEDRON, 1989, 45 (11) :3233-3298
[10]   CHEMISTRY OF FRUIT-FLIES - COMPOSITION OF THE MALE RECTAL GLAND SECRETIONS OF SOME SPECIES OF SOUTH-EAST ASIAN DACINAE - REEXAMINATION OF DACUS-CUCURBITAE (MELON FLY) [J].
PERKINS, MV ;
KITCHING, W ;
DREW, RAI ;
MOORE, CJ ;
KONIG, WA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (04) :1111-1117