Diastereoselective synthesis of cyclic beta(2,3)-amino acids utilizing 4-substituted-1,3-oxazinan-6-ones

Author(s): Sleebs, BE; Nguyen, NH; Hughes, AB;
Details: Publication Year 2013-07-29,Volume 69,Issue #30,Page 6275-6284
Journal Title: TETRAHEDRON
Publication Type: Journal Article
Abstract: 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.
Publisher: PERGAMON-ELSEVIER SCIENCE LTD
Keywords: BETA-AMINO-ACIDS; STEREOSELECTIVE-SYNTHESIS; ALPHA-AMINO; ASYMMETRIC-SYNTHESIS; MEDICINAL CHEMISTRY; ENANTIOSELECTIVE SYNTHESIS; DERIVATIVES; PEPTIDES; METHYL; GAMMA
Research Division(s): Chemical Biology
Publisher's Version: https://doi.org/10.1016/j.tet.2013.05.016

Creation Date: 2013-07-29 12:00:00