Phosphine-catalyzed divergent domino processes between γ-substituted allenoates and carbonyl-activated alkenes

Highly enantioselective and chemodivergent domino reactions between gamma-substituted allenoates and activated alkenes have been developed. In the presence of NUSIOC-Phos, triketone enone substrates smoothly reacted with gamma-substituted allenoates to form bicyclic furofurans in good yields with high stereoselectivities. Alternatively, the reaction between diester-activated enone substrates and gamma-substituted allenoates formed chiral conjugated 1,3-dienes in good yields with excellent enantioselectivities. Notably, by employing substrates with subtle structural difference, under virtually identical reaction conditions, we were able to access two types of chiral products, which are of biological relevance and synthetic importance.

Automated summary

Highly enantioselective and chemodivergent domino reactions have been developed between gamma-substituted allenoates and activated alkenes. Different types of chiral products, with biological relevance and synthetic importance, can be obtained by controlling the structural differences of the substrates under virtually identical reaction conditions.