Stereoselective Synthesis of Indolyl‑<i>C</i>‑glycosides Enabled by Sequential Aminopalladation and Heck Glycosylation of 2‑Alkynylanilines with Glycals

Abstract

An efficient and general approach for the synthesis of indolyl-C-glycosides via aminopalladation and subsequent Heck-type glycosylation of easily available 2-alkynylanilines and glycals has been developed. This protocol features excellent stereoselectivity, a broad substrate scope, and mild reaction conditions. In addition, 2,3-pseudoglycals also successfully participated in this cascade reaction, affording C2/C3-branched indolyl glycosides with high regio-/stereoselectivity. The utility of this protocol was also demonstrated by a large-scale reaction and diversified synthetic transformations of the desired products

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