146861-22-5Relevant articles and documents
Enantioselective synthesis of cyclic, quaternary oxonitriles
Guenes, Yakup,Polat, M. Fatih,Sahin, Ertan,Fleming, Fraser F.,Altundas, Ramazan
supporting information; experimental part, p. 7092 - 7098 (2010/12/24)
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.
A New Entry to 1,3-Polyols, 2-Amino 1,3-Polyols, and β-(1-Hydroxyalkyl)isoserines Using Azetidinone Frameworks as Chiral Templates via Iterative Asymmetric Cycloaddition Reactions
Palomo, Claudio,Aizpurua, Jesus M.,Urchegui, Raquel,Garcia, Jesus M.
, p. 1646 - 1648 (2007/10/02)
A new entry to polyfunctional compounds based on an iterative asymmetric cycloaddition reaction of ketenes to O-protected α-hydroxy aldehyde derived imines is described for the first time.
