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Abstract The conversion of β-amido esters to β-enamino esters is an indispensable step for some synthetic approaches to alkaloids and related medicines. Known methods for such transformation are not only… Click to show full abstract
Abstract The conversion of β-amido esters to β-enamino esters is an indispensable step for some synthetic approaches to alkaloids and related medicines. Known methods for such transformation are not only stepwise, but also proceed with low atom-efficiency. Herein, we report a direct and versatile approach that features the Ir-catalyzed chemoselective reduction of β-amido esters with 1,1,3,3-tetramethyldisiloxane (TMDS). In addition, a lack of some signals was observed in the 13C NMR spectra of some alicyclic β-enamino esters. This revealed a longstanding existing but being ignored phenomenon in the literature.
Journal Title: Tetrahedron
Year Published: 2019
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