A novel propargylic electrophile-induced tandem intermolecular addition-semipinacol rearrangement was developed efficiently under mild conditions. Various allylic silylether substrates as well as Co-complexed propargylic species were applicable to this protocol and gave a series of synthetically useful β-propargyl spirocyclic ketones in moderate to good yields. Its synthetic application was also demonstrated by an efficient construction of the key tricyclic moiety of daphlongamine E.
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Cation-Induced Molecular Switching Based on Reversible Modulation of Peptoid Conformational States.
J Org Chem
October 2018
Department of Chemistry and Biology "A. Zambelli" , University of Salerno, Via Giovanni Paolo II, 132 , Fisciano , Salerno 84084 , Italy.
Peptoids are oligomers of N-substituted glycines with predictable folding and strong potentials as guest-binding receptor molecules. In this contribution, we investigate the structural features of a series of designed symmetric cyclic octamer peptoids (with methoxyethyl/propargyl side chains) as free hosts and reveal their morphologic changes in the presence of sodium and alkylammonium guests as tetrakis[3,5-bis(trifluoromethyl)phenyl]borate salts, reporting the first case of reversible adaptive switching between defined conformational states induced by cationic guests (Na and benzylammonium ion) in the peptoid field. The reported results are based on H NMR data, theoretical models, and single-crystal X-ray diffraction analysis.
View Article and Find Full Text PDFA novel propargylic electrophile-induced tandem intermolecular addition-semipinacol rearrangement was developed efficiently under mild conditions. Various allylic silylether substrates as well as Co-complexed propargylic species were applicable to this protocol and gave a series of synthetically useful β-propargyl spirocyclic ketones in moderate to good yields. Its synthetic application was also demonstrated by an efficient construction of the key tricyclic moiety of daphlongamine E.
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