TRANSITION-METAL MEDIATED ASYMMETRIC-SYNTHESIS .15. DIRECTING GROUP COMPETITION IN ORGANOIRON INTERMEDIATES IN THE SYNTHESIS OF (+/-)-O-METHYLJOUBERTIAMINE

被引:42
作者
STEPHENSON, GR [1 ]
FINCH, H [1 ]
OWEN, DA [1 ]
SWANSON, S [1 ]
机构
[1] GLAXO GRP RES LTD,WARE SG12 0DJ,HERTS,ENGLAND
关键词
D O I
10.1016/S0040-4020(01)87274-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Directing groups work first in concert and then in competition to control the introduction of aryl and 2-dimethylaminoethyl groups by a sequence of two nucleophile additions to cationic tricarbonyl(eta5-cyclohexadienyl)iron(1+) intermediates in a synthesis of O-methyljoubertiamine that employs an iterative approach. This synthesis provides an example of the successful use of directing group competition to effect the reversal of undesired directing effects in target oriented applications of electrophilic pi-complexes.
引用
收藏
页码:5649 / 5662
页数:14
相关论文
共 81 条
[21]   ORGANOIRON COMPLEXES IN ORGANIC-SYNTHESIS - A FACILE TMS MEDIATED DECARBOXYLATION OF ORGANOIRON COMPLEXES [J].
CHANDLER, M ;
PARSONS, PJ ;
MINCIONE, E .
TETRAHEDRON LETTERS, 1983, 24 (51) :5781-5784
[22]   SYNTHESIS AND ELECTROPHILIC REACTIVITY OF DICARBONYLNITROSYL(CYCLOHEXADIENYL)MANGANESE CATIONS - DOUBLE NUCLEOPHILIC-ADDITION TO COORDINATED ARENES [J].
CHUNG, YK ;
SWEIGART, DA ;
CONNELLY, NG ;
SHERIDAN, JB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (08) :2388-2393
[23]  
CORSS PE, 1966, THESIS U MANCHESTER
[24]   (ETA-5-1-SUBSTITUTED-PENTADIENYL) (TRICARBONYL)IRON(+1) CATIONS - REACTIVITY WITH MALONATE NUCLEOPHILES [J].
DONALDSON, WA ;
RAMASWAMY, M .
TETRAHEDRON LETTERS, 1988, 29 (12) :1343-1346
[25]   REACTION OF BENZOCYCLOBUTADIENEDICARBONYLNITROSYLIRON HEXAFLUOROPHOSPHATE WITH R3M (M=P, AS - R=ME, PH) - NOVEL EXAMPLE OF A NUCLEOPHILIC ADDITION SUBSTITUTION REACTION [J].
EFRATY, A ;
LIEBMAN, D ;
SIKORA, J ;
DENNEY, DZ .
INORGANIC CHEMISTRY, 1976, 15 (04) :886-889
[26]   STEREOSELECTIVE SYNTHESES OF SOME CYCLOHEXENE DERIVATIVES USING COMPLEXES OF MOLYBDENUM [J].
FALLER, JW ;
MURRAY, HH ;
WHITE, DL ;
CHAO, KH .
ORGANOMETALLICS, 1983, 2 (03) :400-409
[27]   APPLICATIONS OF SUBSTITUTED ARYLACETALDEHYDES IN THE TOTAL SYNTHESIS OF SECO-MESEMBRANE ALKALOIDS .1. THE TOTAL SYNTHESIS OF (+/-)-0-METHYLJOUBERTIAMINE [J].
FORBES, CP ;
SCHOEMAN, WJ ;
STRAUSS, HF ;
VENTER, EMM ;
WENTELER, GL ;
WIECHERS, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (04) :906-910
[28]  
HASSNER A, 1978, TETRAHEDRON LETT, P4475
[29]   APPROACHES TO ENANTIOSELECTIVE SYNTHESES USING TRICARBONYL(DIENE)IRON COMPLEXES [J].
HOWELL, JAS ;
THOMAS, MJ .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1983, (07) :1401-1409
[30]  
HUDSON RD, UNPUB