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Nickel-Catalyzed Regio- and Enantioselective Aminolysis of 3,4-Epoxy Alcohols

Journal of the American Chemical Society, ISSN: 1520-5126, Vol: 137, Issue: 13, Page: 4308-4311
2015
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The first catalytic regio- and enantioselective aminolysis of 3,4-epoxy alcohols has been accomplished. Under the catalysis of Ni(ClO4)2·6H2O, the C4 selective ring opening of various 3,4-epoxy alcohols proceeded in a stereospecific manner with high regioselectivities. Furthermore, with the Ni-BINAM catalytic system the enantioselective ring opening of 3,4-epoxy alcohols furnished various γ-hydroxy-δ-amino alcohols as products with complete regiocontrol and high enantioselectivities (up to 94% ee).

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