Efficient syntheses of both enantiomers of a spirodiamine diester from (L)- and (D)-aspartic acid are described. The key transformation was the conversion of Boc-protected t-butyl aspartate into the derived aldehyde, two directional Horner Emmons olefination, hydrogenation and selective acid-catalyzed Boc-deprotection and spirocyclization. An alternative, two-directional approaches to derivatives of 1,7-diazaspiro[5.5]undecane is described.