ASYMMETRIC-SYNTHESIS OF BICYCLO[4.3.0]NONAN-8-ONES BY INTRAMOLECULAR PAUSON-KHAND REACTION

被引:44
作者
CASTRO, J
MOYANO, A
PERICAS, MA
RIERA, A
GREENE, AE
机构
[1] UNIV BARCELONA,DEPT QUIM ORGAN,MARTI FRANQUES 1-11,E-08028 BARCELONA,SPAIN
[2] UNIV J FOURIER,LEDSS,F-38041 GRENOBLE,FRANCE
关键词
D O I
10.1016/S0957-4166(00)86192-3
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The intramolecular Pauson-Khand reaction of (E)-1-alkoxy-1-octen-7-ynes derived from (1S,2R)-2-phenylcyclohexanol is described. 7-Alkoxybicyclo[4.3.0]non-1(9)-en-8-ones are obtained in yields up to 65% and with diastereoselectivities higher than 10:1. The absolute configuration of the major diastereomer obtained has been ascertained and can be rationalized on the basis of the preferential conformation of the precursor.
引用
收藏
页码:307 / 310
页数:4
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共 35 条
  • [31] N-OXIDE PROMOTED PAUSON-KHAND CYCLIZATIONS AT ROOM-TEMPERATURE
    SHAMBAYATI, S
    CROWE, WE
    SCHREIBER, SL
    [J]. TETRAHEDRON LETTERS, 1990, 31 (37) : 5289 - 5292
  • [32] NEW ROUTE TO THE SYNTHESIS OF POLYCYCLIC COMPOUNDS BASED ON A STEPWISE ADE-REACTION OF DICOBALT HEXACARBONYL COMPLEXES OF CONJUGATED ENYNES WITH A SUBSEQUENT INTRAMOLECULAR KHAND-PAUSON TYPE REACTION
    SMIT, WA
    GYBIN, AS
    SHASHKOV, AS
    STRYCHKOV, YT
    KYZMINA, LG
    MIKAELIAN, GS
    CAPLE, R
    SWANSON, ED
    [J]. TETRAHEDRON LETTERS, 1986, 27 (11) : 1241 - 1244
  • [33] DIVERGENT STEREOSELECTIVE SYNTHESIS OF (E) AND (Z) O-ALKYL ENOL ETHERS
    SOLA, L
    CASTRO, J
    MOYANO, A
    PERICAS, MA
    RIERA, A
    [J]. TETRAHEDRON LETTERS, 1992, 33 (20) : 2863 - 2866
  • [34] CAMPHOR-DERIVED ALCOHOLS AS CHIRAL AUXILIARIES FOR ASYMMETRIC PAUSON-KHAND BICYCLIZATIONS - ENANTIOSELECTIVE SYNTHESIS OF ALPHA-METHOXYENONES
    VERDAGUER, X
    MOYANO, A
    PERICAS, MA
    RIERA, A
    GREENE, AE
    PINIELLA, JF
    ALVAREZLARENA, A
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1992, 433 (03) : 305 - 310
  • [35] VERDAGUER X, IN PRESS J AM CHEM S