Synthesis of beta-amino esters by regioselective amination of allyl bromides with aryl and alkyl amines

Abstract

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 S(N)2' product 7 was produced using dichloromethane as a solvent and triethylamine (7 equiv) as base; S(N)2 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.