From isoxazolidines to tetrahydro-1,3-oxazines for the synthesis of chiral pyrrolidines

[EN] A novel approach for the synthesis of chiral tetrasubstituted pyrrolidines has been developed. The rearrangement of isoxazolidines into tetrahydro-1,3-oxazines using reactive organic bromides is herein described for the first time. The subsequent opening reaction of these tetrahydro-1,3-oxazines with nucleophiles probes the usefulness of the method for the synthesis of biologically active compounds.The authors gratefully acknowledge the help of A. Lithgow (NMR) and C. Raposo (MS) of Universidad de Salamanca; FSE, MICINN CTQ2009-11172BQU, Junta de Castilla and Leon for financial support. MFF is grateful to the JCyL for her fellowship.García García, P. (2012). From isoxazolidines to tetrahydro-1,3-oxazines for the synthesis of chiral pyrrolidines. RSC Advances. 2(29):11040-11048. https://doi.org/10.1039/c2ra22110a110401104822