Enantioselective intramolecular alkene hydroaminations catalyzed by yttrium complexes of axially chiral bis(thiolate) ligands

被引:180
作者
Kim, JY [1 ]
Livinghouse, T [1 ]
机构
[1] Montana State Univ, Dept Chem, Bozeman, MT 59717 USA
关键词
D O I
10.1021/ol050294z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A yttrium(III) complex derived from proligand 7c has been shown to be a superior catalyst for enantioselective intramolecular alkene hydroaminations that provide cyclic amines with ee's ranging from 69% to 89%.
引用
收藏
页码:1737 / 1739
页数:3
相关论文
共 18 条
[1]   CHIRAL LEWIS-ACID CATALYZED ASYMMETRIC NUCLEOPHILIC RING-OPENING OF CYCLOHEXENE OXIDE [J].
ADOLFSSON, H ;
MOBERG, C .
TETRAHEDRON-ASYMMETRY, 1995, 6 (08) :2023-2031
[2]   ORTHO-LITHIOTHIOPHENOL EQUIVALENTS - GENERATION, REACTIONS, AND APPLICATIONS IN SYNTHESIS OF HINDERED THIOLATE LIGANDS [J].
BLOCK, E ;
ESWARAKRISHNAN, V ;
GERNON, M ;
OFORIOKAI, G ;
SAHA, C ;
TANG, K ;
ZUBIETA, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (02) :658-665
[3]   Lanthanide complexes derived from (R)-1,1′-binaphthyl-2,2′-bis(neopentylamine) -: {Li(THF)4}{Ln[(R)-C20H12N2(C10H22)]2} (Ln = Sm, Yb) -: novel catalysts for enantioselective intramolecular hydroamination [J].
Collin, J ;
Daran, JC ;
Schulz, E ;
Trifonov, A .
CHEMICAL COMMUNICATIONS, 2003, (24) :3048-3049
[4]   C2-symmetric ansa-lanthanidocene complexes.: Synthesis via silylamine elimination and β-SiH agostic rigidity [J].
Eppinger, J ;
Spiegler, M ;
Hieringer, W ;
Herrmann, WA ;
Anwander, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (13) :3080-3096
[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]   Kinetic resolution of chiral aminoalkenes via asymmetric hydroamination/cyclisation using binaphtholate yttrium complexes [J].
Gribkov, DV ;
Hultzsch, KC .
CHEMICAL COMMUNICATIONS, 2004, (06) :730-731
[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]  
Kim Y. K., 2002, ANGEW CHEM, V114, P3797
[10]   Chelating bis(thiophosphinic amidate)s as versatile supporting ligands for the group 3 metals. An application to the synthesis of highly active catalysts for intramolecular alkene hydroamination [J].
Kim, YK ;
Livinghouse, T ;
Horino, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (32) :9560-9561