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Protected syn-aldol compounds from direct, catalytic, and enantioselective reactions of N-acyl-1,3-oxazinane-2-thiones with aromatic acetals
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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]NiCl2, 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.
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MELLADO HIDALGO, Miguel, et al. Protected syn-aldol compounds from direct, catalytic, and enantioselective reactions of N-acyl-1,3-oxazinane-2-thiones with aromatic acetals. Organic Letters. 2023. Vol. 23, num. 4, pags. 659-664. ISSN 1523-7060. [consulted: 30 of June of 2026]. Available at: https://hdl.handle.net/2445/196206