Palladium-catalyzed ring-forming aminoacetoxylation of alkenes

被引：366
作者：
Alexanian, EJ [1 ]
Lee, C [1 ]
Sorensen, EJ [1 ]
机构：
[1] Princeton Univ, Dept Chem, Princeton, NJ 08544 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 21期
关键词：
D O I：
10.1021/ja051406k
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A mild, palladium(II)-catalyzed ring-forming aminoacetoxylation of alkenes is described. Treatment of a range of nitrogen nucleophiles with catalytic palladium(II) in the presence of PhI(OAc)2 as oxidant resulted in alkene aminoacetoxylation, affording a variety of nitrogen-containing heterocycles. Our studies indicate the possibility for high levels of reaction regio- and stereocontrol. It appears that this is a stereoselective trans alkene difunctionalization and thus a useful alternative to related cis-selective, metal-catalyzed alkene aminohydroxylation processes. Copyright © 2005 American Chemical Society.
引用
收藏
页码：7690 / 7691
页数：2
相关论文
共 28 条
[1]  
BACKVALL JE, 1980, J ORG CHEM, V45, P2893
[2]   PALLADIUM IN SOME SELECTIVE OXIDATION REACTIONS [J].
BACKVALL, JE .
ACCOUNTS OF CHEMICAL RESEARCH, 1983, 16 (09) :335-342
[3]  
BACKVALL JE, 1975, TETRAHEDRON LETT, V16, P2225
[4]   The synthesis of vicinal amino alcohols [J].
Bergmeier, SC .
TETRAHEDRON, 2000, 56 (17) :2561-2576
[5]  
Block E., 1991, COMPREHENSIVE ORGANI, P329, DOI DOI 10.1016/B978-0-08-052349-1.00097-4
[6]   The Sharpless asymmetric aminohydroxylation [J].
Bodkin, JA ;
McLeod, MD .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (24) :2733-2746
[7]   Aerobic oxidative amination of unactivated alkenes catalyzed by palladium [J].
Brice, JL ;
Harang, JE ;
Timokhin, VI ;
Anastasi, NR ;
Stahl, SS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (09) :2868-2869
[8]   Palladium-catalyzed oxygenation of unactivated sp3 C-H bonds [J].
Desai, LV ;
Hull, KL ;
Sanford, MS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (31) :9542-9543
[9]   A highly selective catalytic method for the oxidative functionalization of C-H bonds [J].
Dick, AR ;
Hull, KL ;
Sanford, MS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (08) :2300-2301
[10]   The tethered aminohydroxylation (TA) reaction [J].
Donohoe, TJ ;
Johnson, PD ;
Pye, RJ .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (12) :2025-2028
123