Halogenated salt assisted Cu-catalyzed asymmetric 1,4-borylstannation of 1,3-enynes: enantioselective synthesis of allenylstannes |
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| Authors: | Jialin Ye Yang Liao Hao Huang Yang Liu Dongmei Fang Min Wang Lianrui Hu Jian Liao |
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| Institution: | College of Chemical Engineering, Sichuan University, Chengdu 610065 China ; Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041 China.; University of Chinese Academy of Sciences, Beijing 10049 China ; School of Science and Research Center for Advanced Computation, Xihua University, Chengdu 610039 China, |
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| Abstract: | An enantioselective 1,4-borylstannation of 1,3-enynes employed a chiral sulfoxide phosphine (SOP)/Cu complex as a catalyst, and the desired products, chiral allenylstannes, were first synthesized by asymmetric catalysis with satisfactory yields and enantioselectivies. In this protocol, a catalytic amount of additive, a halogenated salt, plays a crucial role in the success. Control experiments and theoretical studies disclosed that the four-membered ring transmetallation transition states which were stabilized by a halide anion are the key to yields and stereochemical outcomes.An enantioselective 1,4-borylstannation of 1,3-enynes employed a chiral sulfoxide phosphine (SOP)/Cu complex as a catalyst, and the desired products, chiral allenylstannes, were first synthesized by asymmetric catalysis with satisfactory yields and enantioselectivies. |
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