Towards peptide versions of Cram's host-guest chemistry: The synthesis of Cα,α-disubstituted glycines with binaphthol-based crowned side-chains

Article abstract of DOI:10.1016/S0040-4039(03)00127-8

Dietherification of the hydroxy groups of various α,α-disubstituted α-amino acids or their precursors, possessing either an achiral frame derived from α-hydroxymethylserine, or a 2,2′,6,6′-tetrasubstituted biphenyl frame with only an axial chirality, or a frame with α-carbon chirality derived from α-methyl-(L)-DOPA, using (R)-2,2′-bis-(5-tosyloxy-3-oxa-1-pentyloxy)-1,1′-binaphthyl as alkylating agent, gave a new series of amino acids bearing binaphthol-based crown-ethers, as building blocks for the construction of short-chain peptide helices with topologically well-localized receptors.