Phosphine-catalyzed divergent domino processes between γ-substituted allenoates and carbonyl-activated alkenes |
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| Authors: | Mingyue Wu Zhaobin Han Huanzhen Ni Nengzhong Wang Kuiling Ding Yixin Lu |
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| Institution: | Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543 Singapore.; State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 China, |
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| 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.Highly enantioselective and chemodivergent domino reactions between γ-substituted allenoates and activated alkenes have been developed. |
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