"1434-193X" . "We describe a polymer-supported stereoselective synthesis of the (1S,5S)-6-oxa-3,8-biazabicyclooctane-bridged scaffold by tandem iminium ion cyclization/nucleophilic addition reactions. A series of resin-bound acyclic intermediates bearing different substituents were prepared, and the scope and limitations of the chemical route leading to the bridged scaffold were evaluated. The Thr-derived bridged scaffold was found to be substantially more stable in acid than the Ser-derived scaffold, which was partially transformed into dihydropyrazinones. Substitution at the iminium-forming nitrogen was critical for acid stability, and the N-arylsulfonamides with electron-withdrawing groups yielded the highest purity of the crude products prepared by acid-mediated cleavage. The acid-labile target compounds were synthesized by nucleophile-mediated cleavage from the esterified Wang resin and cyclization in formic acid." . . "RIV/61989592:15310/13:33147692" . "[E3691D894F27]" . . . "P(EE2.3.20.0009), P(GAP207/12/0473), P(ME09057)" . . . "We describe a polymer-supported stereoselective synthesis of the (1S,5S)-6-oxa-3,8-biazabicyclooctane-bridged scaffold by tandem iminium ion cyclization/nucleophilic addition reactions. A series of resin-bound acyclic intermediates bearing different substituents were prepared, and the scope and limitations of the chemical route leading to the bridged scaffold were evaluated. The Thr-derived bridged scaffold was found to be substantially more stable in acid than the Ser-derived scaffold, which was partially transformed into dihydropyrazinones. Substitution at the iminium-forming nitrogen was critical for acid stability, and the N-arylsulfonamides with electron-withdrawing groups yielded the highest purity of the crude products prepared by acid-mediated cleavage. The acid-labile target compounds were synthesized by nucleophile-mediated cleavage from the esterified Wang resin and cyclization in formic acid."@en . "000320173900023" . "Zaj\u00ED\u010Dek, Jaroslav" . . "European Journal of Organic Chemistry" . "15" . . . "Oliver, Allen G" . . . . "Polymer-Supported Stereoselective Synthesis of (1S,5S)-6-Oxa-3,8-diazabicyclooctanes"@en . "2"^^ . . "Sch\u00FCtznerov\u00E1, Eva" . "4"^^ . "Polymer-Supported Stereoselective Synthesis of (1S,5S)-6-Oxa-3,8-diazabicyclooctanes" . . "Bicyclic compounds; Solid-phase synthesis; Nucleophilic addition; Heterocycles; Peptidomimetics"@en . . "RIV/61989592:15310/13:33147692!RIV14-GA0-15310___" . "8"^^ . . "2013" . . "Polymer-Supported Stereoselective Synthesis of (1S,5S)-6-Oxa-3,8-diazabicyclooctanes"@en . . "15310" . . . "10.1002/ejoc.201300093" . "DE - Spolkov\u00E1 republika N\u011Bmecko" . "Krch\u0148\u00E1k, Viktor" . "Polymer-Supported Stereoselective Synthesis of (1S,5S)-6-Oxa-3,8-diazabicyclooctanes" . . . "97092" .