260975-31-3Relevant academic research and scientific papers
Highly Enantioselective Ferrocenyl Palladacycle-Acetate Catalysed Arylation of Aldimines and Ketimines with Arylboroxines
Schrapel, Carmen,Frey, Wolfgang,Garnier, Delphine,Peters, René
supporting information, p. 2448 - 2460 (2017/02/23)
Benzylic N-substituted stereocenters constitute a frequent structural motif in drugs. Their highly enantioselective generation is hence of technical importance. An attractive strategy is the arylation of imines with organoboron reagents. Chiral Rh complexes have reached a high level of productivity for this reaction type. In this article we describe that an electron rich PdIIcatalyst also performs well in the arylation of aldimines, comparable to the best Rh catalysts. The ferrocenyl palladacycle-acetate catalyst allows for a broad substrate scope and very high enantioselectivities. Commonly observed side reactions like aryl–aryl homocouplings and imine hydrolysis could be blocked. Mechanistic studies implicate that a) the acetate ligand is crucial for transmetallation, b) the active catalyst is most likely a palladacycle-OAc monomer, c) the rate limiting step is probably the product release. By added KOAc the arylation could also be applied to ketimines.
Exogenous-Base-Free Palladacycle-Catalyzed Highly Enantioselective Arylation of Imines with Arylboroxines
Schrapel, Carmen,Peters, Ren
supporting information, p. 10289 - 10293 (2015/09/01)
Enantiomerically pure benzylic amines are important for the development of new drugs. A readily accessible planar-chiral ferrocene-derived palladacycle is shown to be a highly efficient catalyst for the formation of N-substituted benzylic stereocenters; t
Racemic N-sulfonyloxaziridines as highly diastereoselective enolate hydroxylating agents: Enantioselective synthesis of (2S,3S)-3-amino-N- cyclopropyl-2-hydroxyhexanamide
Kiss, Eleonóra,Markó, István E.,Guillaume, Michel
, p. 9173 - 9178 (2011/12/01)
A new, highly enantioselective synthesis of (2S,3S)-3-amino-N-cyclopropyl- 2-hydroxyhexanamide, a synthetic fragment of the experimental hepatitis C drug Telaprevir, has been described. Conjugate addition of the enantiomerically pure Davies lithium amide
Triarylmethyl chlorides as novel, efficient, and mild organic catalysts for the synthesis of N-sulfonyl imines under neutral conditions
Khalafi-Nezhad, Ali,Parhami, Abolfath,Zare, Abdolkarim,Shirazi, Amir Nasrolahi,Zare, Ahmad Reza Moosavi,Hassanimejad, Alireza
, p. 456 - 461 (2008/09/20)
A highly efficient procedure for the preparation of N-sulfonyl imines via condensation of sulfonamides with aldehydes as well as ketones in the presence of triarylmethyl chlorides as metal-free organo-catalysts at 40 °C is described. The advantages of thi
Diastereoselective addition of enantiopure lithium tert- butylsulfinylferrocene to imines
Grach, Guillaume,Santos, Jana Sopkova-De Oliveira,Lohier, Jean-Francois,Mojovic, Ljubica,Ple, Nelly,Turck, Alain,Reboul, Vincent,Metzner, Patrick
, p. 9572 - 9579 (2007/10/03)
(S)-terf-Butylsulfinylferrocene was submitted to ortho-metalation, and the corresponding lithium derivative was trapped by alkyl or aryl imines bearing various electron-withdrawing groups on the nitrogen atom (Ts, Dpp, Boc). New aminosulfoxides were obtai
A general method for the preparation of N-sulfonyl aldimines and ketimines
García Ruano, José Luis,Alemán, José,Cid, M. Belén,Parra, Alejandro
, p. 179 - 182 (2007/10/03)
(Chemical Equation Presented) A simple procedure to obtain N-sulfonyl imines involving the condensation of carbonyl compounds with p-tolyl or tert-butyl sulfinamides followed by oxidation with m-CPBA of the resulting N-sulfinylimines is reported. The meth
An easy synthesis of aliphatic and aromatic N-sulfonyl aldimines
Chemla, Fabrice,Hebbe, Virginie,Normant, Jean-F.
, p. 75 - 77 (2007/10/03)
N-Arenesulfonyl aldimines were prepared from aliphatic and aromatic aldehydes in a two-step transformation.
