Abstract
The title reaction was investigated for both achiral and α-chiral alkenes 1–3, and for cyclic and acyclic nitrones 4 and 8. In each case, addition to allyldiphenylphosphine oxide 1 gave a single isoxazolidine product. The configurations of these isoxazolidines (5 and 9) were investigated by NMR methods, and found to be consistent with reaction via exo transition states. Nitrone additions to α-chiral α-diphenylphosphinoyl alkenes 2 and 3 gave two diastereoisomeric products in all cases studied. The configurations of these isoxazolidines (6, 7, 10, 11) were assigned by analogy with the achiral cases, and also by analogy with the addition of nitrite oxides to the same alkenes. In one case (6a) this was confirmed by chemical conversion. This conversion also demonstrated the potential of this method for the synthesis of 2-(alk-2′-enyl)piperidines, e.g. 17, having defined double-bond geometry.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
