Kinetic resolution of chiral aminoalkenes via asymmetric hydroamination/cyclisation using binaphtholate yttrium complexes

被引:111
作者
Gribkov, DV [1 ]
Hultzsch, KC [1 ]
机构
[1] Univ Erlangen Nurnberg, Inst Organ Chem, D-91054 Erlangen, Germany
关键词
D O I
10.1039/b316096c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Chiral binaphtholate yttrium aryl complexes are highly active and enantioselective catalysts for the asymmetric hydroamination of aminoalkenes, as well as the kinetic resolution of cc-substituted 1-aminopent-4-enes to give trans-2,5-disubstituted pyrrolidines with good enantiomeric excess and high k(rel).
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页码:730 / 731
页数:2
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共 23 条
[1]   Advances and adventures in amination reactions of olefins and alkynes [J].
Beller, M ;
Breindl, C ;
Eichberger, M ;
Hartung, CG ;
Seayad, J ;
Thiel, OR ;
Tillack, A ;
Trauthwein, H .
SYNLETT, 2002, (10) :1579-1594
[2]   ON THE SYNTHESIS OF MONOPENTAMETHYLCYCLOPENTADIENYL DERIVATIVES OF YTTRIUM, LANTHANUM, AND CERIUM [J].
BOOIJ, M ;
KIERS, NH ;
HEERES, HJ ;
TEUBEN, JH .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 364 (1-2) :79-86
[3]   Widening the roof: Synthesis and characterization of new chiral C1-symmetric octahydrofluorenyl organolanthanide catalysts and their implementation in the stereoselective cyclizations of aminoalkenes and phosphinoalkenes [J].
Douglass, Michael R. ;
Ogasawara, Masamichi ;
Hong, Sukwon ;
Metz, Matthew V. ;
Marks, Tobin J. .
Organometallics, 2002, 21 (02) :283-292
[4]   ORGANOLANTHANIDE-CATALYZED HYDROAMINATION - A KINETIC, MECHANISTIC, AND DIASTEREOSELECTIVITY STUDY OF THE CYCLIZATION OF N-UNPROTECTED AMINO OLEFINS [J].
GAGNE, MR ;
STERN, CL ;
MARKS, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (01) :275-294
[5]   CHIRAL ORGANOLANTHANIDES DESIGNED FOR ASYMMETRIC CATALYSIS - A KINETIC AND MECHANISTIC STUDY OF ENANTIOSELECTIVE OLEFIN HYDROAMINATION/CYCLIZATION AND HYDROGENATION BY C-1-SYMMETRICAL ME(2)SI(ME(4)C(5))(C(5)H(3)R-ASTERISK)LN COMPLEXES WHERE R-ASTERISK=CHIRAL AUXILIARY [J].
GIARDELLO, MA ;
CONTICELLO, VP ;
BRARD, L ;
GAGNE, MR ;
MARKS, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (22) :10241-10254
[6]   The asymmetric hetero-Diels-Alder reaction of enamide aldehydes with Danishefsky's diene and an efficient synthesis of chiral binaphthyl ligands [J].
Gong, LZ ;
Pu, L .
TETRAHEDRON LETTERS, 2000, 41 (14) :2327-2331
[7]   Synthesis and characterization of new biphenolate and binaphtholate rare-earth-metal amido complexes: Catalysts for asymmetric olefin hydroamination/cyclization [J].
Gribkov, DV ;
Hultzsch, KC ;
Hampell, F .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (19) :4796-4810
[8]   C2-symmetric bis(oxazolinato)lanthanide catalysts for enantioselective intramolecular hydroamination/cyclization [J].
Hong, SW ;
Tian, S ;
Metz, MV ;
Marks, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (48) :14768-14783
[9]   Highly stereoselective intramolecular hydroamination/cyclization of conjugated aminodienes catalyzed by organolanthanides [J].
Hong, SW ;
Marks, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (27) :7886-7887
[10]  
Kim Y. K., 2002, ANGEW CHEM, V114, P3797