Protected <i>syn</i>-Aldol Compounds from Direct, Catalytic, and Enantioselective Reactions of <i>N</i>-Acyl-1,3-oxazinane-2-thiones with Aromatic Acetals
Miguel Mellado‐Hidalgo, Elias A. Romero-Cavagnaro, Sajanthanaa Nageswaran, Sabrina Puddu, Stuart C. D. Kennington, Anna M. Costa, Pedro Romea, Fèlix Urpı́, Gabriel Aullón, Mercè Font‐Bardía
Abstract
High Resolution Image Download MS PowerPoint Slide A direct and asymmetric syn -aldol reaction of N -acyl-1,3-oxazinane-2-thiones with dialkyl acetals from aromatic acetals in the presence of 2–5 mol % [DTBM-SEGPHOS]NiCl 2, TMSOTf, and lutidine has been developed. It has been established that the oxazinanethione heterocycle, used for the first time as a scaffold in asymmetric carbon–carbon bond-forming reactions, can be smoothly removed to give access to a variety of enantiomerically pure compounds with high synthetic value.
Topics & Concepts
ChemistryAldol reactionEnantioselective synthesisCatalysisOrganic chemistryReaction conditionsCarbon fibersMaterials scienceComposite materialComposite numberAsymmetric Synthesis and CatalysisSynthesis and Catalytic ReactionsSynthesis of β-Lactam Compounds