Dynamic kinetic asymmetric [3 + 2] annulation reactions of aminocyclopropanes
We report the first example of a dynamic kinetic asymmetric [3 + 2] annulation reaction of aminocyclopropanes with both enol ethers and aldehydes. Using a Cu catalyst and a commercially available bisoxazoline ligand, cyclopentyl- and tetrahydrofurylamines were obtained in 69-99% yield and up to a 98:2 enantiomeric ratio using the same reaction conditions. The method gives access to important enantio-enriched nitrogen building blocks for the synthesis of bioactive compounds.
De Nanteuil, Florian,Serrano, Eloisa,Perrotta, Daniele,Waser, Jerome
supporting information
p. 6239 - 6242
(2014/05/20)
Synthesis of aminocyclobutanes by iron-catalyzed [2+2] cycloaddition
Fab Four: An iron-catalyzed [2+2] cycloaddition furnishes aminocyclobutanes with a broad range of substituents in excellent yields and diastereoselectivities. The products can be obtained on a gram scale and can be further converted to β-peptide derivatives in a few steps. Furthermore, a [4+2] cycloaddition between an aminocyclobutane and an olefin leads to the corresponding cyclohexylamines. Copyright
De-Nanteuil, Florian,Waser, Jerome
supporting information
p. 9009 - 9013
(2013/09/02)
Process for production of cyclic N-vinyl carboxylic acid amide
There is provided a process for producing a cyclic N-vinyl carboxylic acid amide stably in safety and low cost, using, as starting raw materials, a cyclic carboxylic acid ester and monoethanolamine both available inexpensively and easily. The process comprises subjecting a cyclic carboxylic acid ester and monoethanolamine to an intermolecular dehydration reaction (a first-step reaction) in a liquid phase to produce a cyclic N-(2-hydroxyethyl) carboxylic acid amide and then subjecting the cyclic N-(2-hydroxyethyl) carboxylic acid amide to an intramolecular dehydration reaction (a second-step reaction) in a gas phase in the presence of an oxide catalyst containing an alkali metal element and/or an alkaline earth metal element and silicon, to produce a cyclic N-vinyl carboxylic acid amide.
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(2008/06/13)
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