Asymmetric synthesis of quaternary aryl amino acid derivatives via a three-component aryne coupling reaction

作者：Jones Elizabeth P; Jones Peter; White Andrew J P; Barrett Anthony G M^*

来源：Beilstein Journal of Organic Chemistry, 2011, 7: 1570-1576.

DOI：10.3762/bjoc.7.185

• aryl amino acids
• arynes
• asymmetric
• multicomponent
• quaternary

A method was developed for the synthesis of alpha-alkyl, alpha-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.

• 出版日期2011-11-25