期刊
TETRAHEDRON
卷 69, 期 30, 页码 6275-6284出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2013.05.016
关键词
beta-Amino acid; 1,3-Oxazinan-6-one; Ring closing metathesis; Enolate chemistry; N-Methyl amino acids
资金
- La Trobe University
- NHMRC [1010326]
The 4-substituted-1,3-oxazinan-6-one scaffold is a versatile synthon enabling access to a diverse array of beta-amino acid derivatives. In this study, the synthetic utility of the 1,3-oxazinan-6-one is expanded to include the diastereoselective synthesis of cyclic beta(2,3)-amino acids. Enolate chemistry is used to first alkylate the 4-vinyl, 4-allyl, and 4-butenyl oxazinan-6-ones with various alkenyl electrophiles, in high dr. The resulting 4,5-bis-alkene adducts are then transformed into 4,5-cyclic-1,3-oxazinan-6-ones utilizing the ring closing metathesis reaction. The metathesis products are subsequently converted into a variety of five-, six-, and seven-membered cyclic beta(2,3)-amino acids. The research further highlights the 1,3-oxazinan-6-one as a versatile synthon for producing beta-amino acid derivatives. (C) 2013 Elsevier Ltd. All rights reserved.
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