Cobalt(I)-catalyzed asymmetric [2+2+2] cycloaddition of alkynes and nitriles: Synthesis of enantiomerically enriched atropoisomers of 2-arylpyridines

被引:233
作者
Gutnov, A
Heller, B
Fischer, C
Drexler, HJ
Spannenberg, A
Sundermann, B
Sundermann, C
机构
[1] Univ Rostock eV, Leibniz Inst Organ Katalyse, D-18055 Rostock, Germany
[2] Univ Rostock eV, Leibniz Inst Organ Katalyse, D-52099 Aachen, Germany
关键词
asymmetric catalysis; atropoisomerism; cobalt; cyclotrimerization; nitrogen heterocycles;
D O I
10.1002/anie.200454164
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new flavor of chiral induction in the [2+2+2] cycloaddition yielding pyridines: Atropoisomers were prepared in the reaction of alkynes and nitriles in the presence of 1 mol % chiral Co1 catalysts such as 1 with high yields and up to 93% ee.
引用
收藏
页码:3795 / 3797
页数:3
相关论文
共 31 条
[1]   SYNTHESIS AND RESOLUTION OF 1-(2-DIPHENYLPHOSPHINO-1-NAPHTHYL)ISOQUINOLINE - A P-N CHELATING LIGAND FOR ASYMMETRIC CATALYSIS [J].
ALCOCK, NW ;
BROWN, JM ;
HULMES, DI .
TETRAHEDRON-ASYMMETRY, 1993, 4 (04) :743-756
[2]   ENANTIOSELECTIVE CATALYSIS BY 1-(1-ISOQUINOLINVL)-2-NAPHTHALENEMETHANOL - AN ATROPISOMERICALLY CHIRAL N-O CHELATING LIGAND [J].
BAKER, RW ;
REA, SO ;
SARGENT, MV ;
SCHENKELAARS, EMC ;
SKELTON, BW ;
WHITE, AH .
TETRAHEDRON-ASYMMETRY, 1994, 5 (01) :45-48
[3]   ORGANOCOBALT COMPOUNDS IN THE SYNTHESIS OF PYRIDINES - AN EXAMPLE OF STRUCTURE-EFFECTIVITY RELATIONSHIPS IN HOMOGENEOUS CATALYSIS [J].
BONNEMANN, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (04) :248-262
[4]  
Bonnemann H., 1985, ANGEW CHEM, V97, P264
[5]  
Brunner H, 1999, SYNTHESIS-STUTTGART, P429
[6]   Enantiomerically pure 1-(2-methoxy-1-naphthyl) and 1-(2-methylthio-1-naphthyl)isoquinoline: two new axially chiral N-O and N-S ligands for asymmetric catalysis [J].
Chelucci, G ;
Bacchi, A ;
Fabbri, D ;
Saba, A ;
Ulgheri, F .
TETRAHEDRON LETTERS, 1999, 40 (03) :553-556
[7]   Synthesis and resolution of 1,1-bi-8-methylisoquinoline: Formation of an optically active complex with high chiral recognition [J].
Chelucci, G ;
Cabras, MA ;
Saba, A ;
Sechi, A .
TETRAHEDRON-ASYMMETRY, 1996, 7 (04) :1027-1032
[8]  
Grotjahn D. B, 1995, COMPREHENSIVE ORGANO, V12, P741
[9]   Syntheses of chiral nonracemic half-sandwich cobalt complexes with menthyl-derived cyclopentadienyl, indenyl, and fluorenyl ligands [J].
Gutnov, A ;
Drexler, HJ ;
Spannenberg, A ;
Oehme, G ;
Heller, B .
ORGANOMETALLICS, 2004, 23 (05) :1002-1009
[10]   Tartrate-derived cyclopentadienes for the synthesis of chiral substituted (η5-cyclopentadiene)(η4-cycloocta-1,5-diene)cobalt(I) complexes [J].
Gutnov, A ;
Heller, B ;
Drexler, HJ ;
Spannenberg, A ;
Oehme, G .
ORGANOMETALLICS, 2003, 22 (07) :1550-1553