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Literature DB >> 16637627

The oxidative mannich reaction catalyzed by dirhodium caprolactamate.

Arthur J Catino¹, Jason M Nichols, Brian J Nettles, Michael P Doyle.

Abstract

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 gamma-aminoalkyl butenolides are obtained.

Entities: Chemical

Mesh：

Substances：
Rhodium

Year: 2006 PMID： 16637627 PMCID： PMC2610808 DOI： 10.1021/ja061146m

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

9 in total

1. Chiral heterocycles by iminium ion cyclization.

Authors: Jacques Royer; Martine Bonin; Laurent Micouin
Journal: Chem Rev Date: 2004-05 Impact factor: 60.622

2. Ruthenium-catalyzed oxidative cyanation of tertiary amines with hydrogen peroxide and sodium cyanide.

Authors: Shun-Ichi Murahashi; Naruyoshi Komiya; Hiroyuki Terai
Journal: Angew Chem Int Ed Engl Date: 2005-10-28 Impact factor: 15.336

Review 3. Synthetic approaches towards structurally diverse gamma-butyrolactone natural-product-like compounds.

Authors: Michael Seitz; Oliver Reiser
Journal: Curr Opin Chem Biol Date: 2005-06 Impact factor: 8.822

4. Highly efficient copper-catalyzed nitro-Mannich type reaction: cross-dehydrogenative-coupling between sp3 C-H bond and sp3 C-H bond.

Authors: Zhiping Li; Chao-Jun Li
Journal: J Am Chem Soc Date: 2005-03-23 Impact factor: 15.419

5. An approach to the skeleton of the securinega alkaloids. The total synthesis of (+/-)-securinine.

Authors: S Liras; J E Davoren; J Bordner
Journal: Org Lett Date: 2001-03-08 Impact factor: 6.005

Review 6. Evolution of the vinylogous Mannich reaction as a key construction for alkaloid synthesis.

Authors: Stephen F Martin
Journal: Acc Chem Res Date: 2002-10 Impact factor: 22.384

7. Benzylic oxidation catalyzed by dirhodium(II,III) caprolactamate.

Authors: Arthur J Catino; Jason M Nichols; Hojae Choi; Sidhartha Gottipamula; Michael P Doyle
Journal: Org Lett Date: 2005-11-10 Impact factor: 6.005

8. Dirhodium(II) caprolactamate: an exceptional catalyst for allylic oxidation.

Authors: Arthur J Catino; Raymond E Forslund; Michael P Doyle
Journal: J Am Chem Soc Date: 2004-10-27 Impact factor: 15.419

9. Aerobic ruthenium-catalyzed oxidative cyanation of tertiary amines with sodium cyanide.

Authors: Shun-Ichi Murahashi; Naruyoshi Komiya; Hiroyuki Terai; Takahiro Nakae
Journal: J Am Chem Soc Date: 2003-12-17 Impact factor: 15.419

9 in total

12 in total

The oxidative mannich reaction catalyzed by dirhodium caprolactamate.

1. Chiral heterocycles by iminium ion cyclization.

2. Ruthenium-catalyzed oxidative cyanation of tertiary amines with hydrogen peroxide and sodium cyanide.

Review 3. Synthetic approaches towards structurally diverse gamma-butyrolactone natural-product-like compounds.

4. Highly efficient copper-catalyzed nitro-Mannich type reaction: cross-dehydrogenative-coupling between sp3 C-H bond and sp3 C-H bond.

5. An approach to the skeleton of the securinega alkaloids. The total synthesis of (+/-)-securinine.

Review 6. Evolution of the vinylogous Mannich reaction as a key construction for alkaloid synthesis.

7. Benzylic oxidation catalyzed by dirhodium(II,III) caprolactamate.

8. Dirhodium(II) caprolactamate: an exceptional catalyst for allylic oxidation.

9. Aerobic ruthenium-catalyzed oxidative cyanation of tertiary amines with sodium cyanide.

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2. B(C₆F₅)₃-Catalyzed C-H Alkylation of N-Alkylamines Using Silicon Enolates without External Oxidant.

3. Perspective on dirhodium carboxamidates as catalysts.

4. Site-Selective α-C-H Functionalization of Trialkylamines via Reversible Hydrogen Atom Transfer Catalysis.

5. Iridium(I)-Catalyzed α-C(sp³)-H Alkylation of Saturated Azacycles.

6. Photoredox Activation and Anion Binding Catalysis in the Dual Catalytic Enantioselective Synthesis of β-Amino Esters.

7. α-Arylation of Saturated Azacycles and N-Methylamines via Palladium(II)-Catalyzed C(sp(3))-H Coupling.

8. Remote Oxidation of Aliphatic C-H Bonds in Nitrogen-Containing Molecules.

9. Cyclization reactions through DDQ-mediated vinyl oxazolidinone oxidation.

10. Remodeling of fumagillol: discovery of an oxygen-directed oxidative Mannich reaction.