A 1 M solution of LiHMDS (2.2 mL) in hexanes was added slowly to a solution containing 0.5 g (2 mmol) of triethyl-4-phosphonocrotonate in 10 mL of THF at 0 o C under an argon atmosphere. After 0.5 h a solution containing 0.28 g (2.01 mmol) of 7-indolizidone (12) in 2 mL of THF was added and the mixture was stirred overnight. The mixture was diluted with 70 mL of diethyl ether and stirred with 5 mL of saturated NH4Cl (aq). The layers were separated, and the organic layer was dried over anhydrous K2CO3 and the solvent was removed under reduced pressure to provide 0.22 g of a mixture of geometric isomers of 14. EIMS m/z 235 (62, M + ), , 162 (29), 176 (28), 162 (34), 160 (11), 83 (100), 81 (53), 70 (24). The crude mixture was taken up in 20 mL of EtOH and treated with 1 mL of 10% HCl, and hydrogenated over 40 mg of 10% Pd/C at 3 atm pressure for 45 min. The mixture was filtered through celite and after removal of the solvent partitioned between diethyl ether and 10% NaOH (aq). The organic layer was dried over anhydrous K2CO3, the solvent was removed from the ether solution to provide 0.19 g of the saturated amine ester (16) as a 2:1 mixture of isomers.