Synthesis of (beta)-Amino Esters by Regioselective Amination of Allyl Bromides with Aryl and Alkyl Amines

One of the two possible regioisomers can be exclusively formed by combining a suitable solvent and a specific amount of triethylamine as a base during the amination of allyl bromide 5. The SN2ʹ product 7 was produced using dichloromethane as a solvent and triethylamine (7 equiv) as base; SN2 product 6 was predominantly generated in hexane with 0.5 equivalents of triethylamine. Furthermore, a new reaction condition for the efficient cyclization of 7 to yield (alpha)-methylene (beta)-lactam 8 using Sn[N(TMS)2]2 as a reagent, is disclosed.