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Regioselectivity in Lewis acids catalyzed X-H (O, S, N) insertions of methyl styryldiazoacetate with benzyl alcohol, benzyl thiol, and aniline
Authors:Yongli Yue  Yuanhua Wang
Affiliation:a Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, and Graduate School of Chinese Academy of Sciences, Beijing, China
b Department of Chemistry, East China Normal University, Shanghai 200062, China
Abstract:Different from Rh(II) catalysts, X-H (X = O, S, N) insertion of methyl styryldiazoacetate catalyzed by Lewis acids including Cu(I), Cu(II) and Ag(I) complexes occurred at γ-position preferably. Only (E)-isomer was observed in the reactions. This method provides an alternative for the synthesis of γ-hydroxyl or γ-amino acid derivatives.
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