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Enantio- and Diastereoselective Spiroketalization Catalyzed by Chiral Iridium Complex
- Hamilton, James Y., Rössler, Simon L., Carreira, Erick M.
- Journal of the American Chemical Society 2017 v.139 no.24 pp. 8082-8085
- carbonates, diastereoselectivity, iridium
- Iridium–(P,olefin) complex-catalyzed enantio- and diastereoselective formation of substituted spiroketals from racemic, allylic carbonates is reported, which enables the installation of multiple stereogenic centers in a single operation. The protocol was effective for the preparation of a collection of spiroketals of various ring sizes and substituents, including heteroatoms with high enantio- and diastereoselectivity. Furthermore, cascade reactions that couple this enantio- and diastereoselective transformation to additional reversible processes have been achieved to exert concomitant stereocontrol over additional stereogenic centers.