363152-43-6Relevant articles and documents
Organocatalytic asymmetric nitrocyclopropanation of α,β-unsaturated aldehydes
Vesely, Jan,Zhao, Gui-Ling,Bartoszewicz, Agnieszka,Córdova, Armando
, p. 4209 - 4212 (2008)
A novel organocatalytic highly enantioselective nitrocyclopropanation reaction of α,β-unsaturated aldehydes is presented. The 1-nitro-2-formylcyclopropane derivatives synthesized from this catalytic transformation were converted to the corresponding β-nitromethyl-acid esters, which are excellent precursors of GABA analogues such as Baclofen, by subsequent organocatalytic chemoselective ring-opening.
Asymmetric synthesis of functionalized pyrrolizidines by an organocatalytic and pot-economy strategy
Lin, Chia-Hsin,Hong, Bor-Cherng,Lee, Gene-Hsiang
, p. 8243 - 8247 (2016/02/05)
An efficient method has been developed for the enantioselective synthesis of tetrahydro-1H-pyrrolizin-3(2H)-ones starting from α,β-unsaturated aldehydes via a sequence of asymmetric Michael-oxidative esterification-Michal-reduction-reductive amination-lactamization reactions with high enantioselectivities (93-97% ee). The six-step reaction sequence can be conducted with the pot-economy synthetic strategy with only a one-step purification. The structure and absolute stereochemistry of the intermediates and products were confirmed by X-ray analyses of appropriate products.
Asymmetric synthesis of γ-nitroesters by an organocatalytic one-pot strategy
Jensen, Kim L.,Poulsen, Pernille H.,Donslund, Bjarke S.,Morana, Fabio,Jorgensen, Karl Anker
, p. 1516 - 1519 (2012/06/05)
An enantioselective synthesis of γ-nitroesters by a one-pot asymmetric Michael addition/oxidative esterification of α,β- unsaturated aldehydes is presented. The procedure is based on merging the enantioselective organocatalytic nitroalkane addition with an N-bromosuccinimide-based oxidation. The γ-nitroesters are obtained in good yields and enantioselectivities, and the method provides an attractive entry to optically active γ-aminoesters, 2-piperidones, and 2-pyrrolidones.