Pd-catalyzed direct functionalization of glycals with cycloalkenones: application to the synthesis of chiral phenanthrenones

Abstract

A palladium-catalyzed direct C-H functionalization of glycals with cycloalkenones is described and a series of C-2 functionalized glycols were synthesized efficiently with cyclic enones. The direct C-H functionalization of glycals...

Reactivity Switch in Glycal Dienes toward Different Nucleophiles: Mechanistic Insight and Applications toward the Synthesis of Naphthalene-Fused Pyran Derivatives

“…The products were purified by column chromatography on silica gel (100−200 mesh) using hexane/ethyl acetate as the eluent to obtain the pure products. 1 H and 13 C NMR spectra were recorded using 400−600 MHz spectrometers with TMS as the internal standard. Chemical shifts are expressed in parts per million (δ ppm).…”

Site-Selective Lewis Acid Mediated Transformation of Pseudo Glycals to 1-Deoxy-2-thioaryl/alkyl Glycosides

“…The utilization of TMSOTf instead of BF 3 •OEt 2 proved comparable and provided the desired product with an 85% yield. On changing solvents such as DCE and CH 3 CN lesser yields were recorded (Table 1, entries 15,16).…”

“…14 Despite the development towards the synthesis of C2 thioaryl glycals, there is space to improve the current methodologies by avoiding the use of metals, stoichiometric phosphines, and elevated temperature. In continuation of our research on the functionalization of glycals using C2-position, [15][16][17] we were curious to utilize the pseudoglycals having a double bond at the C2/3 position of glycals towards the synthesis of C2-functionalized thioglycosides (Scheme 1).…”

One‐Pot Access to Sulfonyl 2,3‐Diarylnaphthalenes via tBuOK‐Mediated Benzannulation of o‐Bis‐sulfonylmethyl Arenes with Diarylacetylenes

“…; [10c] and (4) NiBr 2 (dppe)‐catalyzed Danheiser benzannulation of pyrazole‐conjugated iodoarene with 2 equivalents of alkynes, as discussed by Thavaselvan and Parthasarathy [10d] . Other annulation routes to Diels–Alder addition of vinyl/aryl glycals and arynes have been proven to synthesize diverse naphthalenes [10e–f] . However, synthesis of 2,3‐diarylnaphthalenes with a sulfonyl group via formal (4+2) benzannulation of o ‐bis‐sulfonylmethyl arenes with diarylacetylenes has not been reported to the best of our knowledge.…”