Synthesis of chiral 1,5-disubstituted pyrrolidinones via electrophile-induced cyclization of 2-(3-butenyl)oxazolines derived from (1R,2S)- and (1S,2R)-norephedrine |
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| Institution: | 1. Institute of Pharmaceutical Chemistry, University of Szeged, PO Box 427, H-6701 Szeged, Hungary;2. Department of Chemistry, University of Jyväskylä, PO Box 35, 40351 Jyväskylä, Finland;3. Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium;1. Département de Chimie, Pavillon Roger Gaudry, Université de Montréal, CP 6128, succ. Centre-ville, Montréal, Québec, Canada H3C 3J7;2. Laboratoire de caractérisation photophysique des matériaux conjugués, Département de Chimie, Pavillon J. A. Bombardier, Université de Montréal, CP 6128, succ. Centre-ville, Montréal, Québec, Canada H3C 3J7;1. School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing, 210023, China;2. MaAnShan High-Tech Research Institute of Nanjing University, MaAnShan, 238200, China;3. Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, Paseo Manuel Lardizábal 3, 20018 San Sebastián, Spain;4. IKERBASQUE, Basque Foundation for Science, Alameda Urquijo 36-5, Plaza Bizkaia, 48011 Bilbao, Spain |
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| Abstract: | Starting from (1R,2S)- and (1S,2R)-norephedrine, enantiomers of the corresponding 2-(3-butenyl)oxazolines were prepared in a two-step process. The cyclization of the intermediate alkenylamides with phenylselenyl bromide afforded cyclic imidates instead of the expected pyrrolidinones. The electrophile-induced cyclizations of 2-alkenyloxazolines with bromine or iodine produced diastereomeric mixtures of chiral 1,5-disubstituted pyrrolidinones. The ring closure of the all-cis (1R,2S,5R)-diastereomer 7 with NaH resulted in the tetrahydropyrrolo2,1-b]oxazol-5-one derivative 18, which was alternatively prepared by the cyclocondensation of (1R,2S)-norephedrine with levulinic acid. |
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