Asymmetric synthesis of β-fluoroaryl-β-amino acids

Abstract

The conjugate addition of lithium (R)-N-benzyl-N-(α-methylbenzyl)amide to a range of β-fluoroaryl-α,β-unsaturated esters gave the corresponding β-amino esters with high diastereoselectivity and in good isolated yields. Sequential treatment of the resultant β-fluoroaryl-β-amino esters under optimised hydrogenolysis conditions, followed by ester hydrolysis with 2.0M aq HCl, provided access to a range of β-fluoroaryl-β-amino acids in good yield.