6592-19-4Relevant articles and documents
A short route to access oxaspiro[: N,3,3]propellanes
Nassar, Youssef,Piva, Olivier
supporting information, p. 5811 - 5815 (2020/08/21)
Novel access to oxaspiro[n,3,3]propellanes has been developed from bicyclic lactones directly prepared by a photochemical hydroxymethylation or alternatively by a three-step sequence. Thanks to the presence of additional hydroxy- and propargylic groups, a second cyclization catalyzed by silver or bismuth salts, led to the propellane structure which was finally transformed into spiranic derivatives by a Simmons-Smith reaction or condensation with α-ketoesters.
Organocatalytic asymmetric synthesis of functionalized 1,3,5- triarylpyrrolidin-2-ones via an aza-Michael/aldol domino reaction
Joie, Celine,Deckers, Kristina,Enders, Dieter
, p. 799 - 808 (2014/04/03)
The organocatalytic asymmetric synthesis of functionalized 1,3,5-triarylpyrrolidin-2-ones bearing three contiguous stereocenters through an aza-Michael/aldol domino reaction of α-ketoamides with α,β-unsaturated aldehydes is described. The domino products
Asymmetric hydrogenation of α-keto acid derivatives by rhodium-{amidophosphine-phosphinite} catalysts
Carpentier, Jean-Francois,Mortreux, Andre
, p. 1083 - 1099 (2007/10/03)
The enantioselective hydrogenation of several α-keto esters (3a-f, 5a-j), α-keto amides (7a-e) and isatine derivatives (9a-d) with a set of four representative neutral homogeneous rhodium-amidophosphine-phosphinite catalysts has been investigated. Trifluoroacetate-Rh-AMPP catalytic precursors promoted the rapid, efficient synthesis of aliphatic α-hydroxy esters 4a-f in moderate to high enantioselectivities (66-95% eel, in contrast to most aromatic α-hydroxy esters 6a-j (8-81% eel. Best enantioselectivities for α-hydroxy amides 8a-e (85-95% eel and dioxindoIes 10a-d (80-94% eel were obtained with chloro-Rh-AMPP precursors. It is proposed that, contrary to α-keto amides, α-keto esters do not chelate onto the rhodium center and that, in such circumstances, the asymmetric induction is mainly controlled by the steric hindrance around the C=O function.