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Catalytic Enantioselective Synthesis of Highly Functionalized Pentafluorosulfanylated Pyrrolidines

Abstract : The first catalytic asymmetric synthesis of highly functionalized pentafluorosulfanylated pyrrolidines is described. The method, based on a 1,3‐dipolar cycloaddition reaction of aryl and heteroaryl‐substituted glycine Schiff bases with pentafluorosulfanyl acrylic esters, gave access to a broad range of pyrrolidines bearing aryl, naphtyl, and heteroaryl groups. By using Xing‐Phos as a catalyst, the corresponding products were obtained in good yields, good to high regioselectivity, and excellent diastereo‐ and enantioselectivities (up to 98 % ee). This methodology allowed the preparation of enantioenriched SF5 compounds for the first time using an enantioselective approach.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02024540
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Submitted on : Tuesday, February 19, 2019 - 11:11:16 AM
Last modification on : Tuesday, January 4, 2022 - 4:21:17 AM

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Qun Zhao, Thi Minh Ha Vuong, Xing-Fen Bai, Xavier Pannecoucke, Li-Wen Xu, et al.. Catalytic Enantioselective Synthesis of Highly Functionalized Pentafluorosulfanylated Pyrrolidines. Chemistry - A European Journal, Wiley-VCH Verlag, 2018, 24 (21), pp.5644-5651. ⟨10.1002/chem.201706167⟩. ⟨hal-02024540⟩

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