期刊
AMINO ACIDS
卷 48, 期 4, 页码 973-986出版社
SPRINGER WIEN
DOI: 10.1007/s00726-015-2138-3
关键词
Anti-viral (HCV) activity; Asymmetric synthesis; Amino acids; Chirality; Schiff bases
资金
- IKERBASQUE, Basque Foundation for Science
- Basque Government [SAIOTEK S-PE13UN098]
Asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid (vinyl-ACCA) is in extremely high demand due to the pharmaceutical importance of this tailor-made, sterically constrained alpha-amino acid. Here we report the development of an advanced procedure for preparation of the target amino acid via two-step S(N)2 and S(N)2' alkylation of novel axially chiral nucleophilic glycine equivalent. Excellent yields and diastereoselectivity coupled with reliable and easy scalability render this method of immediate use for practical synthesis of (1R,2S)-vinyl-ACCA.
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