Asymmetric Allylic Alkylation in Combination with Ring-Closing Metathesis for the Preparation of Chiral N-Heterocycles

Asymmetric copper-catalyzed allylic substitution with methylmagnesium bromide is employed in combination with ring-closing olefin metathesis or ene-yne metathesis to achieve the synthesis of chiral, unsaturated nitrogen heterocycles. The resulting six- to eight-membered chiral heterocycles are accessible in high yields and with excellent enantioselectivities. Original language English Pages (from-to) 4658-4660 Number of pages 3 Journal Organic letters Volume 12 Issue number 20 DOIs https://doi.org/10.1021/ol101944j Publication status Published - 2010 Keywords NITROGEN-CONTAINING HETEROCYCLES SUBSTITUTION-REACTIONS CONJUGATE ADDITION OLEFIN-METATHESIS GRIGNARD-REAGENTS MANZAMINE-A ALKALOIDS PYRROLIDINE PIPERIDINE AZEPINE