Efficient asymmetric synthesis of N-protected-β-aryloxyamino acids via regioselective ring opening of serine sulfamidate carboxylic acid

Published in: Journal, Article, Research Support, Non-U.S. Gov’t, Volume : 12, Issue : 33, Pages : 6507-6515

DOI : 10.1039/c4ob01047g

Author : Malhotra, Rajesh; Dey, Tushar K.; Dutta, Swarup; Basu, Sourav; Hajra, Saumen

Abstract : First regioselective ring opening of serine derived cyclic sulfamidate by hard nucleophiles like ArONa is developed, where β-elimination of serine sulfamidate ester by stronger nucleophiles is overcome by reversal of the electronic effect of the carboxylate anion. This method provides easy and direct access to a variety of N-Boc- and N-PMB protected β-aryloxy-α-amino acids with complete retention of enantiopurity in moderate to high yields.