Jackson, R.F. orcid.org/0000-0002-6130-808X, Adams, H. and Salih, N. (2016) Synthesis of ω-Oxo Amino Acids and trans-5-Substituted Proline Derivatives using Cross-methathesis of Unsaturated Amino Acids. Journal of Organic Chemistry. ISSN 0022-3263
Abstract
A range of 7-oxo, 8-oxo and 9-oxo amino acids, analogues of 8-oxo-2-aminodecanoic acid, one of the key components of the cyclic tetrapeptide apicidin, has been prepared by a three-step process involving copper-catalysed allylation of serine-, aspartic acid- and glutamic acid-derived organozinc reagents, followed by cross-metathesis of the resulting terminal alkenes with unsaturated ketones, and hydrogenation. The intermediate 7-oxo-5- enones underwent a highly diastereoselective (dr ≥96:4) acid-catalyzed aza-Michael reaction to give trans-2,5-disubstituted pyrrolidines, 5-substituted proline derivatives. The azaMichael reaction was first observed when the starting enones were allowed to stand in solution in deuterochloroform, but can be efficiently promoted by catalytic amounts of dry HCl
Metadata
Item Type: | Article |
---|---|
Authors/Creators: |
|
Copyright, Publisher and Additional Information: | © 2016 American Chemical Society. This is an author produced version of a paper subsequently published in Journal of Organic Chemistry. Uploaded in accordance with the publisher's self-archiving policy. |
Dates: |
|
Institution: | The University of Sheffield |
Academic Units: | The University of Sheffield > Faculty of Science (Sheffield) > Department of Chemistry (Sheffield) |
Funding Information: | Funder Grant number ENGINEERING AND PHYSICAL SCIENCE RESEARCH COUNCIL (EPSRC) EP/L026872/1 |
Depositing User: | Symplectic Sheffield |
Date Deposited: | 18 Aug 2016 08:34 |
Last Modified: | 17 Aug 2017 12:29 |
Published Version: | https://dx.doi.org/10.1021/acs.joc.6b01571 |
Status: | Published |
Publisher: | American Chemical Society |
Refereed: | Yes |
Identification Number: | 10.1021/acs.joc.6b01571 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:103844 |