The oxidative Mannich reaction catalyzed by dirhodium caprolactamate

被引：175

作者：

Catino, AJ ^{[1
]}

Nichols, JM ^{[1
]}

Nettles, BJ ^{[1
]}

Doyle, MP ^{[1
]}

机构：

[1] Univ Maryland, Dept Chem & Biochem, College Pk, MD 20742 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 17期

关键词：

D O I：

10.1021/ja061146m

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Dirhodium caprolactamate [Rh2(cap)4] is a highly effective catalyst for the oxidative Mannich reaction. The reaction proceeds via C-H oxidation of a tertiary amine followed by nucleophilic capture. This green transformation is conducted in protic solvent using inexpensive T-HYDRO (70% t-BuOOH in water). Synthetically valuable γ-aminoalkyl butenolides are obtained. Copyright © 2006 American Chemical Society.

引用

页码：5648 / 5649

页数：2

共 23 条

[1]

[Anonymous], [No title captured]

[2]

Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO

[3]

2-E

[4] Vinylogous Mannich reactions: selectivity and synthetic utility [J].

Bur, SK ;

Martin, SF .

TETRAHEDRON, 2001, 57 (16) :3221-3242

[5] Benzylic oxidation catalyzed by dirhodium(II,III) caprolactamate [J].

Catino, AJ ;

Nichols, JM ;

Choi, H ;

Gottipamula, S ;

Doyle, MP .

ORGANIC LETTERS, 2005, 7 (23) :5167-5170

[6] Dirhodium(II) caprolactamate: An exceptional catalyst for allylic oxidation [J].

Catino, AJ ;

Forslund, RE ;

Doyle, MP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (42) :13622-13623

[7] Highly efficient CuBr-catalyzed cross-dehydrogenative coupling (CDC) between tetrahydroisoquinolines and activated methylene compounds [J].

Li, ZP ;

Li, CJ .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (15) :3173-3176

[8] Highly efficient copper-catalyzed nitro-mannich type reaction:: Cross-dehydrogenative-coupling between sp3 C-H bond and sp3 C-H bond [J].

Li, ZP ;

Li, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (11) :3672-3673

[9] An approach to the skeleton of the Securinega alkaloids.: The total synthesis of (±)-securinine [J].

Liras, S ;

Davoren, JE ;

Bordner, J .

ORGANIC LETTERS, 2001, 3 (05) :703-706

[10] Evolution of the vinylogous Mannich reaction as a key construction for alkaloid synthesis [J].

Martin, SF .

ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (10) :895-904

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