A direct and asymmetric -aldol reaction of -acyl-1,3-oxazinane-2-thiones with dialkyl acetals from aromatic acetals in the presence of 2-5 mol % [DTBM-SEGPHOS]NiCl, 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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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9903318PMC
http://dx.doi.org/10.1021/acs.orglett.2c04254DOI Listing

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