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A mild, practical protocol has been developed for the Suzuki cross-coupling of unprotected thienylsulfonamides from air- and bench-stable organotrifluoroborates in the absence of a protecting group on the sulfonamide nitrogen. The developed synthetic method can be applied to the preparation of various arylated and heteroarylated thienylsulfonamides under… (More)
The first total synthesis of Rolloamide B, a cyclic proline-enriched heptapeptide, is reported. This work features solution phase benzotriazole-mediated peptide synthesis ligating native amino acids.
Benzotriazol-1-yl-sulfonyl azide, a new crystalline, stable, and easily available diazotransfer reagent provides N-(α-azidoacyl)benzotriazoles convenient for N-, O-, C- and S-acylations. The efficient syntheses of various amides, azido protected peptides, esters, ketones and thioesters is reported together with a wide range of azides (including α-azido… (More)
Direct access to complex, enantiopure benzylamine architectures using a synergistic iridium photoredox/nickel cross-coupling dual catalysis strategy has been developed. New C(sp(3))-C(sp(2)) bonds are forged starting from abundant and inexpensive natural amino acids.
Chemical ligation via O- to N-acyl transfer of O-acylated serine containing peptides affords serine containing native peptides via 8- and 11-membered cyclic transition states opening the door to a wide variety of potential applications to peptide elaboration. The feasibility of these traceless chemical ligations is feasible as supported by computation.
An effective protocol toward the O-arylation of β-hydroxy-α-amino acid substrates serine and threonine has been developed via Chan-Lam cross-coupling. This Cu(II)-catalyzed transformation involves benign open-flask conditions that are well-tolerated with a variety of protected (Boc-, Cbz-, Tr-, and Fmoc-) serine and threonine derivatives and various… (More)