Catalytic asymmetric intramolecular hydroamination of aminoalkenes

被引:89
作者
Ogata, Tokutaro [1 ]
Ujihara, Atsushi [1 ]
Tsuchida, Susumu [1 ]
Shimizu, Tomoko [1 ]
Kaneshige, Atsunori [1 ]
Tomioka, Kiyoshi [1 ]
机构
[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
基金
日本学术振兴会;
关键词
D O I
10.1016/j.tetlet.2007.07.117
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Asymmetric intramolecular cyclization of aminoalkenes was catalyzed by a catalytic amount of n-butyllithium, diisopropylamine, and a newly designed chiral bisoxazoline in toluene to produce kinetically controlled exo-cyclized amines with up to 91% ee quantitatively. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6648 / 6650
页数:3
相关论文
共 43 条
[1]   Efficient intramolecular hydroamination of unactivated alkenes catalysed by butyllithium [J].
Ates, A ;
Quinet, C .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (09) :1623-1626
[2]   Anti-Markovnikov-functionalizations of unsaturated compounds part 3 - Base-catalyzed hydroamination of aromatic olefins - An efficient route to 1-aryl-4-(arylethyl)piperazines [J].
Beller, M ;
Breindl, C .
TETRAHEDRON, 1998, 54 (23) :6359-6368
[3]   Intramolecular hydroamination of unactived olefins with Ti(NMe2)4 as a precatalyst [J].
Bexrud, JA ;
Beard, JD ;
Leitch, DC ;
Schafer, LL .
ORGANIC LETTERS, 2005, 7 (10) :1959-1962
[4]   Calcium-mediated intramolecular hydroamination catalysis [J].
Crimmin, MR ;
Casely, IJ ;
Hill, MS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (07) :2042-2043
[5]   The conjugate addition of enantiomerically pure lithium amides as homochiral ammonia equivalents: scope, limitations and synthetic applications [J].
Davies, SG ;
Smith, AD ;
Price, PD .
TETRAHEDRON-ASYMMETRY, 2005, 16 (17) :2833-2891
[6]   N-Allyl-N-tert-butyldimethylsilylamine for chiral ligand-controlled asymmetric conjugate addition to tert-butyl alkenoates [J].
Doi, H ;
Sakai, T ;
Yamada, K ;
Tomioka, K .
CHEMICAL COMMUNICATIONS, 2004, (16) :1850-1851
[7]   Chiral ligand-controlled asymmetric conjugate addition of lithium amides to enoates [J].
Doi, H ;
Sakai, T ;
Iguchi, M ;
Yamada, K ;
Tomioka, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (10) :2886-2887
[8]   Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds [J].
Fagnou, K ;
Lautens, M .
CHEMICAL REVIEWS, 2003, 103 (01) :169-196
[9]   Nucleophilic chiral amines as catalysts in asymmetric synthesis [J].
France, S ;
Guerin, DJ ;
Miller, SJ ;
Lectka, T .
CHEMICAL REVIEWS, 2003, 103 (08) :2985-3012
[10]   A ternary complex reagent for an asymmetric reaction of lithium ester enolates with imines [J].
Fujieda, H ;
Kanai, M ;
Kambara, T ;
Iida, A ;
Tomioka, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (08) :2060-2061