6-O-Picolinyl and 6-O-Picoloyl Building Blocks As Glycosyl Donors with Switchable Stereoselectivity

Organic Letters
Abhijeet K KayasthaA V Demchenko

Abstract

Remote 6-O-picolinyl or 6-O-picoloyl substituents often provide high β-selectivity due to H-bond-mediated aglycone delivery (HAD). Herein it has been demonstrated that if the nitrogen atom of the 6-O-picolinyl or picoloyl moiety is temporarily blocked by coordination to a metal center (Pd), it cannot engage in HAD-mediated β-glycosylation. Hence, the stereoselectivity of 6-O-picolinyl/picoloyl-assisted glycosylations can be "switched" to α-selectivity.

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Citations

Jan 20, 2016·Journal of the American Chemical Society·Peng-Cheng GaoJin-Song Yang
Aug 18, 2016·Journal of the American Chemical Society·Kyan A D'Angelo, Mark S Taylor
Feb 26, 2016·Organic & Biomolecular Chemistry·Jagodige P YasomaneeAlexei V Demchenko
Oct 7, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Susanne Striegler, Jessica B Pickens
Oct 25, 2017·Beilstein Journal of Organic Chemistry·Xiao G Jia, Alexei V Demchenko
Aug 20, 2020·Organic & Biomolecular Chemistry·Catherine AlexAlexei V Demchenko

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