mmol is added neat and the mixture is stirred for 30 min at 78 u00b0 c the mixture is quenched with saturated sodium bicarbonate solution at 78 u00b0 c and then extracted with ether combined ether extracts are dried mgso 4 and concentrated in vacuo the residue is purified by radial plc silica gel hexanes to give 154 mg 72 of product as an off white solid having amp of 90 91 u00b0 c to a vigorously stirred solution of 2 fluoro 4 iodo 3 methylpyridine 100 mg 0 422 mmol prepared according to example 4 in 2 5 ml of thf at 78 u00b0 c under nitrogen is added n buli 2 36m 0 19 ml 0 443 mmol and the mixture is stirred for 1 min a solution of 1r 2s trans 2 u03b1 cumyl cyclohexyl 2 ketobutyrate 140 mg 0 463 mmol in 0 8 ml of thf is added to the reaction mixture after stirring 15 min at 78 u00b0 c the reaction mixture is allowed to warm to room temperature for 15 min the mixture is quenched with saturated sodium bicarbonate solution and extracted with ether the combined ether extracts are dried k 2 co 3 and concentrated in vacuo the residue is purified by radial plc silica gel 1 acetone hexanes 2 acetone hexanes to give 140 mg 80 of product as a colorless oil 94 de as determined by 500 mhz 1 h nmr analysis the other diastereomer could not be separated by radial plc analysis hrms exact mass calculated for c 25 h 32 fno 3 413 2366 m found 413 2376 ir chcl 3 cm 1 2963 2862 1717 1607 1407 1098 1015 1 h nmr cdcl 3 u03b4 7 98 8 00 d 1h j 5 hz 7 15.