期刊
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
卷 7, 期 -, 页码 1570-1576出版社
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.7.185
关键词
aryl amino acids; arynes; asymmetric; multicomponent; quaternary
资金
- EPSRC
- Pfizer
- generous Glaxo Endowment
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.
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