Diastereoselective synthesis of highly functionalized beta(2,2,3)-substituted amino acids from 4-substituted-1,3-oxazinan-6-ones
- Author(s)
- Nguyen, NH; Sleebs, BE; White, JM; Hughes, AB;
- Details
- Publication Year 2012-06-17,Volume 68,Issue #24,Page 4745-4756
- Journal Title
- TETRAHEDRON
- Publication Type
- Journal Article
- Abstract
- 1,3-Oxazinan-6-ones were used to generate substituted beta(2,2,3)-substituted amino acid derivatives. The enolates of 1,3-oxazinan-6-ones were trans-selectively intercepted with electrophiles. This alkylation was subsequently optimized for a one-pot dialkylation to form 5,5-disubstituted oxazinanones. The initial 5-monomethylated compounds could be enolized and then diastereoselectively intercepted with different electrophiles to form differentially 5,5-disubstituted products. The 5,5-dialkylated oxazinanones were then transformed to N-methyl beta(2,2,3)-substituted amino acids by reductive cleavage. Hydrolysis or solvolysis of the oxazinanones afforded beta(2,2,3)-substituted amino acids or esters, respectively. The chemistry thus provides access to a range of symmetrical and stereopure beta(2,2,3)-substituted amino acids and further establishes 1,3-oxazinan-6-ones as useful intermediates. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.
- Publisher
- PERGAMON-ELSEVIER SCIENCE LTD
- Keywords
- BETA-PEPTIDES
- Research Division(s)
- Chemical Biology
- Publisher's Version
- https://doi.org/10.1016/j.tet.2012.04.012
- Terms of Use/Rights Notice
- Crown copyright © 2012 Published by Elsevier Ltd. All rights reserved
Creation Date: 2012-06-17 12:00:00