Palladium-catalyzed ring-forming aminoacetoxylation of alkenes

被引：364

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

页码：7690 / 7691

页数：2

共 28 条

[1] BACKVALL JE, 1980, J ORG CHEM, V45, P2893
[2] PALLADIUM IN SOME SELECTIVE OXIDATION REACTIONS
BACKVALL, JE
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1983, 16 (09) : 335 - 342
[3] BACKVALL JE, 1975, TETRAHEDRON LETT, V16, P2225
[4] The synthesis of vicinal amino alcohols
Bergmeier, SC
[J]. 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
Bodkin, JA
McLeod, MD
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (24): : 2733 - 2746
[7] Aerobic oxidative amination of unactivated alkenes catalyzed by palladium
Brice, JL
Harang, JE
Timokhin, VI
Anastasi, NR
Stahl, SS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (09) : 2868 - 2869
[8] Palladium-catalyzed oxygenation of unactivated sp3 C-H bonds
Desai, LV
Hull, KL
Sanford, MS
[J]. 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
Dick, AR
Hull, KL
Sanford, MS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (08) : 2300 - 2301
[10] The tethered aminohydroxylation (TA) reaction
Donohoe, TJ
Johnson, PD
Pye, RJ
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (12) : 2025 - 2028

← 1 2 3 →