Strong and Confined Acids Control Five Stereogenic Centers in Catalytic Asymmetric Diels–Alder Reactions of Cyclohexadienones with Cyclopentadiene.

Autor: Ghosh, Santanu, Das, Sayantani, Kanta De, Chandra, Yepes, Diana, Neese, Frank, Bistoni, Giovanni, Leutzsch, Markus, List, Benjamin
Předmět:
Zdroj: Angewandte Chemie International Edition; 7/20/2020, Vol. 59 Issue 30, p12347-12351, 5p
Abstrakt: We describe a highly enantioselective Diels–Alder reaction of cross‐conjugated cyclohexadienones with cyclo-pentadiene, in which five stereocenters are effectively controlled by a strongly acidic and confined imidodiphosphorimidate catalyst. Our approach provides tricyclic products in excellent stereoselectivity. We also report methods to convert the obtained products into useful intermediates and a computational study that aids in gaining deeper insight into the reaction mechanism and origin of stereoselectivity. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index