Recently we reported an asymmetric catalytic method for the preparation of cis-a,b-epoxyamides from aldehydes and diazoacetamides with a chiral borate catalyst containing a VANOL ligand. With this it was envisioned that access could be achieved to various 3,4-epoxy-2-piperidone alkaloids starting from the diazoacetamide 1 and aldehydes of the type 2 (Scheme 1). These would include (-)tedanalactam 5, 2 (+)-kausine 6, piplaroxide 7, 2e, 4 epoxydihydropiplartine 8 and epoxypipermethstine 9 . The published syntheses of (-)-tedanalactam 5 have involved starting from the chiral pool (glucose), 2d the use of a chiral auxiliary to effect resolution 2e and in the only asymmetric catalytic approach the use of the Sharpless AD reaction. The published syntheses of (+)-piplaroxide 7 2e and (-)-epoxypipermethystine 9 6b have both used a chiral auxiliary to effect resolution. No syntheses of (+)-kausine 6 or (-)-epoxydihydropiplartine 8 have been reported.