Asymmetric nitroallylation of arylboronic acids with nitroallyl acetates catalyzed by chiral rhodium complexes and its application in a concise total synthesis of optically pure (+)-gamma-lycorane |
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Authors: | Dong Lin Xu Yan-Jun Cun Lin-Feng Cui Xin Mi Ai-Qiao Jiang Yao-Zhong Gong Liu-Zhu |
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Institution: | Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041, China. |
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Abstract: | reaction: see text]A new rhodium-catalyzed highly enantioselective nitroallylation of 2-nitrocyclohex-2-enol esters with arylboronic acids is described. A rhodium complex of RhOH(COD)]2 and optically pure BINAP is the optimal catalyst that provides good yields and high enantioselectivities ranging from 90 to 99% ee for various arylboronic acids at 50 degrees C. A concise total synthesis of optically pure (+)-gamma-lycorane in overall 38% yield was achieved on the basis of this new method. |
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