A preparation of haloalkylidene cyclopentanones

被引:5
作者
Cornwall, NJ [1 ]
Linehan, S [1 ]
Weavers, RT [1 ]
机构
[1] UNIV OTAGO,DEPT CHEM,DUNEDIN,NEW ZEALAND
关键词
D O I
10.1016/S0040-4039(97)00503-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A radical-based 5-exo-dig cyclisation, initiated by addition of a trichloromethyl radical to an acyclic acetylenic ketone with an appropriately positioned double bond, has been employed to produce a variety of cyclic haloalkylidene cyclopentanones in moderate to excellent yields and with a high degree of stereoselectivity for the (E)-isomer. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:2919 / 2922
页数:4
相关论文
共 9 条
[1]   ANTIBIOTICS FROM BASIDIOMYCETES .24. ANTIBIOTICS WITH A REARRANGED HIRSUTANE SKELETON FROM PLEUROTELLUS-HYPNOPHILUS (AGARICALES) [J].
GIANNETTI, BM ;
STEFFAN, B ;
STEGLICH, W ;
KUPKA, J ;
ANKE, T .
TETRAHEDRON, 1986, 42 (13) :3587-3593
[2]   SYNTHESIS OF IODOALKYLIDENE LACTONES FROM ALKENES [J].
HAAIMA, G ;
LYNCH, MJ ;
ROUTLEDGE, A ;
WEAVERS, RT .
TETRAHEDRON, 1993, 49 (20) :4229-4252
[3]   ALKYLIDENE LACTONE SYNTHESIS [J].
HAAIMA, G ;
LYNCH, MJ ;
ROUTLEDGE, A ;
WEAVERS, RT .
TETRAHEDRON, 1991, 47 (28) :5203-5214
[4]   REACTION OF IODOALKYLIDENE LACTONES WITH NUCLEOPHILES [J].
HAAIMA, G ;
MAWSON, SD ;
ROUTLEDGE, A ;
WEAVERS, RT .
TETRAHEDRON, 1994, 50 (11) :3557-3570
[5]   THE RELATIONSHIP BETWEEN PROTON-PROTON NMR COUPLING-CONSTANTS AND SUBSTITUENT ELECTRONEGATIVITIES .1. AN EMPIRICAL GENERALIZATION OF THE KARPLUS EQUATION [J].
HAASNOOT, CAG ;
DELEEUW, FAAM ;
ALTONA, C .
TETRAHEDRON, 1980, 36 (19) :2783-2792
[6]   DICOBALTOCTACARBONYL-MEDIATED CYCLIZATIONS OF ELECTRON-DEFICIENT ALKYNONES [J].
HOYE, TR ;
SURIANO, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (07) :1659-1660
[7]  
LIU ZY, 1990, SYNTHESIS-STUTTGART, P235
[8]   IODOMETHYLENE LACTONE FORMATION - AN IMPROVED SYNTHESIS [J].
MAWSON, SD ;
ROUTLEDGE, A ;
WEAVERS, RT .
TETRAHEDRON, 1995, 51 (16) :4665-4678
[9]   STEREOCHEMICAL COURSE OF AN ENZYME-CATALYZED ALLENE-ACETYLENE ISOMERIZATION [J].
SCHWAB, JM ;
LIN, DCT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (21) :6046-6052