Enantioselective hydroamination/cyclization catalyzed by organolanthanide amide's derived from a new chiral ligand, (S)-2-(pyrrol-2-ylmethyleneamino)-2′-(dimethylamino)-1,1′-binaphthyl

被引:88
作者
Zi, Guofu [1 ]
Xiang, Li [1 ]
Song, Haibin [2 ]
机构
[1] Beijing Normal Univ, Dept Chem, Beijing 100875, Peoples R China
[2] Nankai Univ, Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
关键词
D O I
10.1021/om701058k
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A new series of bis-ligated organolanthanide amides, (1)2-LnN(SiMe3)(2)center dot C7H8 (Ln = Sm (2), Y (3), Yb (4)), have been prepared by the reaction of Ln[N(SiMe3)(2)](3) with the ligand (S)-2-(pyrrol-2-ylmethyleneamino)-2'-(dimethylamino)-1,1'-binaphthyl (1H) in good yields. They are active catalysts for the asymmetric hydroamination/cyclization reaction of aminoalkenes, affording cyclic amines in moderate to good conversions with moderate to good ee values.
引用
收藏
页码:1242 / 1246
页数:5
相关论文
共 72 条
[21]   Group 3 metal complexes based on a chiral tetradentate diamine-diamide ligand:: Synthesis and use in polymerization of (D,L)-lactide and intramolecular alkene hydroamination catalysis [J].
Heck, Romain ;
Schulz, Emmanuelle ;
Collin, Jacqueline ;
Carpentier, Jean-Francois .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 268 (1-2) :163-168
[22]   Development of palladium catalysts for asymmetric hydroamination reactions [J].
Hii, KK .
PURE AND APPLIED CHEMISTRY, 2006, 78 (02) :341-349
[23]   Organolanthanide-catalyzed hydroamination [J].
Hong, S ;
Marks, TJ .
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (09) :673-686
[24]   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
[25]   Palladium-catalyzed intermolecular asymmetric hydroamination with 4,4′-disubstituted BINAP and SEGPHOS [J].
Hu, Aiguo ;
Ogasawara, Masamichi ;
Sakamoto, Takeshi ;
Okada, Atsushi ;
Nakajima, Kiyohiko ;
Takahashi, Tamotsu ;
Lin, Wenbin .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (15) :2051-2056
[26]   Catalytic asymmetric hydroamination of non-activated olefins [J].
Hultzsch, KC .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (10) :1819-1824
[27]   Transition metal-catalyzed asymmetric hydroamination of alkenes (AHA) [J].
Hultzsch, KC .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (2-3) :367-391
[28]   (R)-(+)-2.2′-diamino-1,1′-binaphthyl [J].
Jones, MD ;
Paz, FAA ;
Davies, JE ;
Johnson, BFG .
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2003, 59 :O910-O912
[29]   Internal alkene hydroaminations catalyzed by zirconium(IV) complexes and asymmetric alkene hydroaminations catalyzed by yttrium(III) complexes [J].
Kim, Hyunseok ;
Kim, Young Kwan ;
Shim, Jun Hwan ;
Kim, Misook ;
Han, Mijung ;
Livinghouse, Tom ;
Lee, Phil Ho .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (18) :2609-2618
[30]   Enantioselective intramolecular alkene hydroaminations catalyzed by yttrium complexes of axially chiral bis(thiolate) ligands [J].
Kim, JY ;
Livinghouse, T .
ORGANIC LETTERS, 2005, 7 (09) :1737-1739