Synthesis of N-(2-pyranyl)- and N-cyclohexylindole derivatives via stereoselective addition of indole nucleophiles to organomolybdenum complexes

被引:8
作者
Bjurling, E
Johansson, MH
Andersson, CM
机构
[1] ACADIA Pharmaceut AS, Synthet Chem, DK-2600 Glostrup, Denmark
[2] Univ Lund, Ctr Chem, Dept Quim Organ 1, S-22100 Lund, Sweden
[3] Univ Lund, Ctr Chem, Dept Inorgan Chem 1, S-22100 Lund, Sweden
关键词
D O I
10.1021/om9906060
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Indol-1-yl-substituted dihydropyranyl- and cyclohexenylmolybdenum complexes were obtained via nucleophilic addition of a variety of substituted indoles to cationic (pyran)- and (cyclohexadiene)molybdenum complexes. The efficiency of these addition reactions was found to be highly dependent upon the substitution pattern in the nucleophile. Oxidative decomplexation with iodine smoothly delivered the corresponding allylic iodide in good yield. Complex 6b, was characterized by X-ray crystallography.
引用
收藏
页码:5606 / 5613
页数:8
相关论文
共 33 条
[1]   TRANSITION-METAL MEDIATED ASYMMETRIC-SYNTHESIS .5. ALTERNATIVE METHODS FOR THE FORMATION OF TRICARBONYL(ETA-5-CYCLOHEXADIENYL)IRON(1+) SALTS [J].
ALEXANDER, RP ;
STEPHENSON, GR .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1987, (04) :885-888
[2]   An alternative procedure for preparing cationic η4-diene-molybdenum complexes from the corresponding allylic precursors [J].
Bjurling, E ;
Andersson, CM .
TETRAHEDRON LETTERS, 1999, 40 (10) :1981-1984
[3]   REACTIONS OF COORDINATED LIGANDS .17. SYNTHESIS AND REACTIONS OF CATIONIC ETA-5-INDENYL AND ETA-CYCLOPENTADIENYL-MOLYBDENUM COMPLEXES CONTAINING 1,3-DIENE AND ACETYLENE LIGANDS [J].
BOTTRILL, M ;
GREEN, M .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1977, (23) :2365-2371
[4]  
BRANDENBURG K, 1997, DIAMOND VERSION 2 1
[5]  
Donohoe TJ, 1998, J CHEM SOC PERK T 1, P819
[6]   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
[7]   FUNCTIONALIZATION OF 1,3-DIENES USING CATIONIC COMPLEXES OF MOLYBDENUM [J].
GREEN, M ;
GREENFIELD, S ;
KERSTING, M .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (01) :18-20
[8]   SYNTHESIS AND REACTIONS OF ENANTIOMERICALLY PURE MOLYBDENUM PI-COMPLEXES OF 2H-PYRAN - A GENERAL-APPROACH TO THE ENANTIOSPECIFIC SYNTHESIS OF CIS-2,5-DISUBSTITUTED 5,6-DIHYDRO-2H-PYRANS AND CIS-2,6-DISUBSTITUTED TETRAHYDROPYRANS [J].
HANSSON, S ;
MILLER, JF ;
LIEBESKIND, LS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (26) :9660-9661
[9]   KINETICS OF NUCLEOPHILIC-ATTACK ON COORDINATED ORGANIC MOIETIES .4. MECHANISMS OF ADDITION OF INDOLE AND SUBSTITUTED INDOLES TO TRICARBONYL(CYCLOHEXADIENYL)-IRON AND "CARBONYL(CYCLOHEXADIENYL)-RUTHENIUM CATIONS [J].
KANEMAGUIRE, LAP ;
MANSFIELD, CA .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1976, (21) :2192-2196
[10]  
KENDE AS, 1982, SYNTHETIC COMMUN, V12, P1, DOI 10.1080/00397918208080058