Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 21, Pages 5644-5651Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201706167
Keywords
azomethile ylides; cycloaddition; fluorine; pentafluorosulfanyl; pyrrolidines
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Funding
- INSA Rouen
- Rouen University
- CNRS
- EFRD
- Labex SynOrg [ANR-11-LABX-0029]
- Region Normandie (Crunch Network)
- China Scolarship Council (CSC)
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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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