Diastereoselectivity-switchable and highly enantioselective 1,3-dipolar cycloaddition of nitrones to alkylidene malonates |
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| Authors: | Huang Zheng-Zheng Kang Yan-Biao Zhou Jian Ye Meng-Chun Tang Yong |
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| Affiliation: | State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 200032 Shanghai, China. |
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| Abstract: | Trisoxazoline 1/Co(ClO(4))(2).6H(2)O catalyzed the 1,3-cycloaddition between nitrones 3 with alkylidene malonates 2 at 0 degrees C to give the isoxazolidines with both high enantioselectivity and high exo selectivity. However, when the temperature was lowered from 0 to -40 degrees C, the same cycloaddition afforded endo isomers as the major products with good to high enantioselectivity. A mechanism is provided. |
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