Well-defined and easily accessible yttrium complexes for enantioselective cyclisation of amines tethered to 1,2-di-substituted alkenes

被引:43
作者
Chapurina, Yulia [1 ,2 ]
Hannedouche, Jerome [1 ,3 ]
Collin, Jacqueline [1 ,3 ]
Guillot, Regis [3 ]
Schulz, Emmanuelle [1 ,3 ]
Trifonov, Alexander [2 ]
机构
[1] Univ Paris 11, Equipe Catalyse Mol, ICMMO, UMR 8182, F-91405 Orsay, France
[2] Russian Acad Sci, GA Razuvaev Inst Organomet Chem, Nizhnii Novgorod 603600, Russia
[3] CNRS, F-91405 Orsay, France
关键词
ASYMMETRIC INTRAMOLECULAR HYDROAMINATION; AMIDATE COMPLEXES; CATALYSTS;
D O I
10.1039/c0cc01064b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A straightforward in situ preparation of new chiral amido alkyl ate yttrium complexes is described. They catalysed the enantioselective cyclisation of 1,2-dialkyl-substituted aminopentenes in up to 77% ee, a significant value for this challenging transformation. Complex [(R)-L-0][Y(CH2TMS)(2)center dot Li(THF)(4)] undergoes C-H bond activation resulting in the formation of an original dimeric heterobimetallic yttrium complex which also acts as an active precatalyst.
引用
收藏
页码:6918 / 6920
页数:3
相关论文
共 28 条
[1]   Chiral Amido Alkyl Rare Earth Complexes: A New Family of Asymmetric Intramolecular Hydroamination Catalysts [J].
Aillaud, Isabelle ;
Lyubov, Dmitrii ;
Collin, Jacqueline ;
Guillot, Regis ;
Hannedouche, Jerome ;
Schulz, Emmanuelle ;
Trifonov, Alexander .
ORGANOMETALLICS, 2008, 27 (22) :5929-5936
[2]   New chiral lanthanide amide ate complexes for the catalysed synthesis of scalemic nitrogen-containing heterocycles [J].
Aillaud, Isabelle ;
Collin, Jacqueline ;
Duhayon, Carine ;
Guillot, Regis ;
Lyubov, Dmitrii ;
Schulz, Emmanuelle ;
Trifonov, Alexander .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (07) :2189-2200
[3]   Asymmetric hydroamination of non-activated carbon-carbon multiple bonds [J].
Aillaud, Isabelle ;
Collin, Jacqueline ;
Hannedouche, Jerome ;
Schulz, Emmanuelle .
DALTON TRANSACTIONS, 2007, (44) :5105-5118
[4]   The enantioselective intramolecular aminative functionalization of unactivated alkenes, dienes, allenes and alkynes for the synthesis of chiral nitrogen heterocycles [J].
Chemler, Sherry R. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (15) :3009-3019
[5]   NEW COORDINATION ENVIRONMENTS FOR YTTRIUM FORMED IN-SITU BY HETEROMETALLIC BRIDGING - CRYSTAL-STRUCTURES OF (C(5)H(4)SIME(3))Y[(MU-OCME(3))(MU-ME)ALME(2)](2) AND (ME(3)SICH(2))Y[(MU-CH2)(2)SIME(2)][(MU-OR)LI(THF)(2)](2) [J].
EVANS, WJ ;
BOYLE, TJ ;
ZILLER, JW .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 462 (1-2) :141-148
[6]   STEREOSELECTION EFFECTS IN THE CATALYTIC HYDROAMINATION CYCLIZATION OF AMINOOLEFINS AT CHIRAL ORGANOLANTHANIDE CENTERS [J].
GAGNE, MR ;
BRARD, L ;
CONTICELLO, VP ;
GIARDELLO, MA ;
STERN, CL ;
MARKS, TJ .
ORGANOMETALLICS, 1992, 11 (06) :2003-2005
[7]   Structure-activity relationships for group 4 biaryl amidate complexes in catalytic hydroamination/cyclization of aminoalkenes [J].
Gott, Andrew L. ;
Clarke, Adam J. ;
Clarkson, Guy J. ;
Scott, Peter .
ORGANOMETALLICS, 2007, 26 (07) :1729-1737
[8]   3,3′-bis(trisarylsilyl)-substituted binaphtholate rare earth metal catalysts for asymmetric hydroamination [J].
Gribkov, DV ;
Hultzsch, KC ;
Hampel, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (11) :3748-3759
[9]   Convenient method for the rapid generation of highly active and enantioselective yttrium catalysts for asymmetric hydroamination [J].
Hannedouche, Jerome ;
Aillaud, Isabelle ;
Collin, Jacqueline ;
Schulz, Emmanuelle ;
Trifonov, Alexander .
CHEMICAL COMMUNICATIONS, 2008, (30) :3552-3554
[10]   Intramolecular hydroamination/cyclization of conjugated aminodienes catalyzed by organolanthanide complexes. Scope, diastereo- and enantioselectivity, and reaction mechanism [J].
Hong, S ;
Kawaoka, AM ;
Marks, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (51) :15878-15892