Gold(I)-catalyzed intramolecular hydroamination of alkenyl carbamates

被引:209
作者
Han, XQ [1 ]
Widenhoefer, RA [1 ]
机构
[1] Duke Univ, PM Gross Chem Lab, Durham, NC 27708 USA
关键词
alkenes; amines; gold; homogeneous catalysis; hydroamination;
D O I
10.1002/anie.200600052
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Gold for rings: Reaction of alkenyl carbamates such as 1 in the presence of [Au{P(tBu)2(o-biphenyl)}]Cl and AgOTf led to nitrogen heterocycles (e.g. 2). This AuI-catalyzed intramolecular hydroamination tolerates a range of labile carbamates and substitution patterns and can be applied to the synthesis of bicyclic carbamates and protected piperidines. Cbz = benzyloxycarbonyl. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:1747 / 1749
页数:3
相关论文
共 37 条
[1]   Palladium-catalyzed ring-forming aminoacetoxylation of alkenes [J].
Alexanian, EJ ;
Lee, C ;
Sorensen, EJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (21) :7690-7691
[2]  
Beller M., 2004, TRANSITION METALS OR, V2nd, P403
[3]   Platinum-catalyzed intramolecular hydroamination of unactivated olefins with secondary alkylamines [J].
Bender, CF ;
Widenhoefer, RA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (04) :1070-1071
[4]   A general method for deprotection of N-toluenesulfonyl aziridines using sodium naphthalenide [J].
Bergmeier, SC ;
Seth, PP .
TETRAHEDRON LETTERS, 1999, 40 (34) :6181-6184
[5]  
BROWDER C, 2006, ANGEW CHEM, V118, P1776
[6]  
BROWDER FC, 2006, ANGEW CHEM INT EDIT, V45, P1744
[7]   TETRAHYDROPYRIDONES VIA INTRAMOLECULAR UREIDOMERCURATION [J].
DANISHEFSKY, S ;
TANIYAMA, E ;
WEBB, RR .
TETRAHEDRON LETTERS, 1983, 24 (01) :11-14
[8]  
Fix S. R., 2002, ANGEW CHEM, V114, P172
[9]  
Fix SR, 2002, ANGEW CHEM INT EDIT, V41, P164, DOI 10.1002/1521-3773(20020104)41:1<164::AID-ANIE164>3.0.CO
[10]  
2-B