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Published on: November 9, 2019
Phosphine-catalyzed divergent domino processes between γ-substituted allenoates and carbonyl-activated alkenes
Mingyue Wu1, Zhaobin Han2, Huanzhen Ni1
1Department of Chemistry, National University of Singapore 3 Science Drive 3 Singapore 117543 Singapore chmlyx@nus.edu.sg.
Abstract:
Highly enantioselective and chemodivergent domino reactions between γ-substituted allenoates and activated alkenes have been developed. In the presence of NUSIOC-Phos, triketone enone substrates smoothly reacted with γ-substituted allenoates to form bicyclic furofurans in good yields with high stereoselectivities. Alternatively, the reaction between diester-activated enone substrates and γ-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.
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