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