Enantioselective synthesis of cyclic, quaternary oxonitriles |
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Authors: | Güneş Yakup Polat M Fatih Sahin Ertan Fleming Fraser F Altundas Ramazan |
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Institution: | Department of Chemistry, College of Sciences, Ataturk University, 25240 Erzurum, Turkey. |
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Abstract: | Quaternary oxonitriles are stereoselectively generated from the union of five-, six-, and seven-membered 2-chloroalkenecarbonitriles with chiral alcohols via a Claisen rearrangement. The strategy rests on a new conjugate addition-elimination of allylic alkoxides to 2-chlorocycloalkenecarbonitriles to afford substituted 2-alkoxyalkenenitriles. Subsequent thermolysis unmasks a cyclic oxonitrile while selectively forming a new quaternary center with enantiomeric ratios typically greater than 9:1. The overall alkylation strategy addresses the challenge of enantioselectively generating hindered, quaternary centers while simultaneously installing ketone, nitrile, and olefin functionalities. |
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