The Oxidative Mannich Reaction Catalyzed by Dirhodium Caprolactamate
- 8 April 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (17) , 5648-5649
- https://doi.org/10.1021/ja061146m
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 γ-aminoalkyl butenolides are obtained.Keywords
This publication has 11 references indexed in Scilit:
- Reaction of aromatic amines with Cu(ClO4)2 in acetonitrile as a facile route to amine radical cation generationChemical Physics Letters, 2005
- Synthetic approaches towards structurally diverse γ-butyrolactone natural-product-like compoundsCurrent Opinion in Chemical Biology, 2005
- Highly Efficient Copper-Catalyzed Nitro-Mannich Type Reaction: Cross-Dehydrogenative-Coupling between sp3 C−H Bond and sp3 C−H BondJournal of the American Chemical Society, 2005
- Dirhodium(II) Caprolactamate: An Exceptional Catalyst for Allylic OxidationJournal of the American Chemical Society, 2004
- A New and Simplified Process for Preparing N-[4-(3,4-Dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine and a Telescoped Process for the Synthesis of (1S-cis)-4-(3,4-Dichlorophenol)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine Mandelate: Key Intermediates in the Synthesis of Sertraline HydrochlorideOrganic Process Research & Development, 2004
- An Approach to the Skeleton of the Securinega Alkaloids. The Total Synthesis of (±)-SecurinineOrganic Letters, 2001
- New Developments in the Chemistry of N-Acyliminium Ions and Related IntermediatesTetrahedron, 2000
- The synthetic utility of furan-, pyrrole- and thiophene-based 2-silyloxy dienesChemical Society Reviews, 2000
- Ruthenium-catalyzed oxidation of tertiary amines with hydrogen peroxide in the presence of methanolTetrahedron Letters, 1992
- Ruthenium-catalyzed cytochrome P-450 type oxidation of tertiary amines with alkyl hydroperoxidesJournal of the American Chemical Society, 1988