期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2003, 期 14, 页码 2635-2644出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200300103
关键词
amino acids; synthesis design; nitrogen heterocycles; alpha,beta-didehydroamino acids; dihydrofurans
Carbon nucleophiles, amines, and oxygen nucleophiles were treated with the methyl ester of N-(tert-butoxycarbonyl)-N-(p-tolylsulfonyl)-alpha,beta-didehydroalanine, and also with the methyl esters of N-(tert-butoxycarbonyl)-O-(p-tolylsulfinyl)-alpha,beta-didehydroserine and N-(tert-butoxycarbonyl)-beta-(1,2,4-triazol-1-yl)-alpha,beta-didehydroalanine, both of which were obtained from the former substrate. Carbon nucleophiles of the beta-dicarbonyl type gave furanic amino acids, which were converted into the corresponding pyrrole derivatives (dehydroprolines) in high yields, while use of amines allowed the synthesis of alpha,alpha-diamino acids and beta-amino-alpha,beta-didehydroamino acids. Different types of alkoxyamino acids were obtained by treatment of the above substrates with oxygen nucleophiles. The reactivities of the alpha,beta-didehydroaminobutyric and alpha,beta-didehydrophenylalanine analogues were also tested. Some of the methods developed were applied to the synthesis of cross-linked amino acids, namely didehydrolanthionine and histidino-alpha,beta-didehydroalanine derivatives. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).
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