An intermolecular highly diastereoselective oxa-Michael/Michael type stepwise cycloaddition was developed to synthesize tetrahydropyrans, using an allylic alcohol obtained from Baylis-Hillman reaction and methyl 2-(4-nitrophenyl) acrylate. These molecules were obtained in low to good yields using DBU as a base at 70 °C. This methodology provides a convenient and atom-economical approach for accessing tetrahydropyrans bearing three stereogenic centers, expanding the synthetic applicability and versatility of the oxa-Michael reactions.
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Gutiérrez-Márquez et al. (2024) studied this question.
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