Organocatalytic Oxa-Michael/Michael/Michael/Aldol Condensation Quadruple Domino Sequence : Asymmetric Synthesis of Tricyclic Chromanes
Kumar, M., Chauhan, P., Bailey, S. J., Jafari, E., von Essen, C., Rissanen, K., & Enders, D. (2018). Organocatalytic Oxa-Michael/Michael/Michael/Aldol Condensation Quadruple Domino Sequence : Asymmetric Synthesis of Tricyclic Chromanes. Organic Letters, 20 (4), 1232-1235. doi:10.1021/acs.orglett.8b00175
Published inOrganic Letters
© 2018 American Chemical Society
An efficient and highly stereoselective one-pot, four-component synthesis of functionalized tricyclic chromanes has been achieved through an organocatalyzed quadruple domino reaction. The reaction sequence involves an oxa-Michael/Michael/Michael/aldol condensation between alcohols, 2 equiv of acrolein, and nitrochromenes to generate the pharmaceutically important tricyclic chromanes bearing three contiguous stereogenic centers including a chiral tetrasubstituted carbon center in good domino yields (30–70%) and excellent diastereo- and enantioselectivities (>20:1 dr and >99% ee).