TY - JOUR A1 - Jones, Elizabeth P. A1 - Jones, Peter A1 - White, Andrew J. P. A1 - Barrett, Anthony G. M. T1 - Asymmetric synthesis of quaternary aryl amino acid derivatives via a three-component aryne coupling reaction JF - Beilstein Journal of Organic Chemistry PY - 2011/// VL - 7 SP - 1570 EP - 1576 SN - 1860-5397 DO - 10.3762/bjoc.7.185 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.7.185 KW - aryl amino acids KW - arynes KW - asymmetric KW - multicomponent KW - quaternary N2 - A method was developed for the synthesis of α-alkyl, α-aryl-bislactim ethers in good to excellent yields and high diastereoselectivities, consisting of a facile one-pot procedure in which the aryl group is introduced by means of a nucleophilic addition to benzyne and the alkyl group by alkylation of a resultant benzylic anion. Hydrolysis of the sterically less hindered adducts gave the corresponding quaternary amino acids with no racemization, whereas hydrolytic ring opening gave the corresponding valine dipeptides from bulkier bislactims. ER -