Catalytic Enantioselective Synthesis of Highly Functionalized Pentafluorosulfanylated Pyrrolidines

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...

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Bibliographic Details
Published in:Chemistry : a European journal 2018-04, Vol.24 (21), p.5644-5651
Main Authors: Zhao, Qun, Vuong, Thi Minh Ha, Bai, Xing‐Fen, Pannecoucke, Xavier, Xu, Li‐Wen, Bouillon, Jean‐Philippe, Jubault, Philippe
Format: Article
Language:English
Subjects:
Acrylic esters
Aromatic compounds
Asymmetric synthesis
azomethile ylides
Catalysis
Chemical Sciences
Chemical synthesis
Chemistry
Cycloaddition
Enantiomers
Esters
fluorine
Glycine
Imines
pentafluorosulfanyl
pyrrolidines
Regioselectivity
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Summary: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. Get selective! The first catalytic enantioselective synthesis of highly functionalized pentaflurorosulfanylated pyrrolidines is described. The methodology afforded access to highly functionalized pyrrolidines in good yields, with high regioselectivity and excellent diastereo‐ and enantioselectivities (see scheme).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201706167