133010-06-7Relevant articles and documents
Rapid and column-free syntheses of acyl fluorides and peptides usingex situgenerated thionyl fluoride
Lee, Cayo,Sammis, Glenn M.,Thomson, Brodie J.
, p. 188 - 194 (2021/12/31)
Thionyl fluoride (SOF2) was first isolated in 1896, but there have been less than 10 subsequent reports of its use as a reagent for organic synthesis. This is partly due to a lack of facile, lab-scale methods for its generation. Herein we report a novel protocol for theex situgeneration of SOF2and subsequent demonstration of its ability to access both aliphatic and aromatic acyl fluorides in 55-98% isolated yields under mild conditions and short reaction times. We further demonstrate its aptitude in amino acid couplings, with a one-pot, column-free strategy that affords the corresponding dipeptides in 65-97% isolated yields with minimal to no epimerization. The broad scope allows for a wide range of protecting groups and both natural and unnatural amino acids. Finally, we demonstrated that this new method can be used in sequential liquid phase peptide synthesis (LPPS) to afford tri-, tetra-, penta-, and decapeptides in 14-88% yields without the need for column chromatography. We also demonstrated that this new method is amenable to solid phase peptide synthesis (SPPS), affording di- and pentapeptides in 80-98% yields.
Synthesis and structural characterization of 2:1 [α/aza]-oligomers
Zhou, Zhou,Deng, Cheng,Abbas, Cécile,Didierjean, Claude,Averlant-Petit, Marie-Christine,Bodiguel, Jacques,Vanderesse, Régis,Jamart-Grégoire, Brigitte
, p. 7643 - 7650 (2015/04/22)
The design of a new β-turn inducer is correlated to the discovery of new foldamers. In this paper, we report the liquid phase synthesis of 2:1 [α/aza]-oligomers using a convergent Boc strategy. The NMR, FTIR, restrained molecular dynamics and X-ray diffra
Catalytic enantioselective one-pot aminoborylation of aldehydes: A strategy for construction of nonracemic α-amino boronates
Hong, Kai,Morken, James P.
supporting information, p. 9252 - 9254 (2013/07/26)
We report a strategy for the conversion of aldehydes to enantiomerically enriched α-amino boronates through the intermediacy of in situ-generated silylimines. This transformation is brought about by Pt-catalyzed asymmetric addition of B2(pin)s