HFIP-Mediated, Highly Chemo-, Regio-, and Stereoselective Hydrofunctionalizations of Ynamides: Access to Stereodefined Alkenes Bearing Drugs and Natural Products
Appanapalli N. V. Satyanarayana,
Tanmay Chatterjee
Abstract:We disclose a sustainable and versatile
synthetic strategy
for
the highly chemo-, regio-, and stereoselective hydrofunctionalizations
of ynamides, through its activation by a solvent, HFIP, to access
a wide variety of stereodefined ketene N,N, N,O, N,S, and N,Se acetals
in high yield at room temperature. The reaction proceeded through
the formation of the reactive keteniminium ion intermediate, formed
via protonation at the β-carbon of ynamide by HFIP, followed
by an attack of a nucleophile (syn-addition) at t… Show more
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