Exploring the scope of asymmetric synthesis of β-Hydroxy-γ-lactams via Noyori-type reductions
| dc.contributor.author | Lynch, Denis | |
| dc.contributor.author | Deasy, Rebecca E. | |
| dc.contributor.author | Clarke, Leslie-Ann | |
| dc.contributor.author | Slattery, Catherine N. | |
| dc.contributor.author | Khandavilli, Udaya Bhaskara Rao | |
| dc.contributor.author | Lawrence, Simon E. | |
| dc.contributor.author | Maguire, Anita R. | |
| dc.contributor.author | Magnus, Nicholas A. | |
| dc.contributor.author | Moynihan, Humphrey A. | |
| dc.contributor.funder | Enterprise Ireland | en |
| dc.contributor.funder | Eli Lilly and Company | en |
| dc.date.accessioned | 2016-12-01T10:15:32Z | |
| dc.date.available | 2016-12-01T10:15:32Z | |
| dc.date.issued | 2016-09-22 | |
| dc.date.updated | 2016-11-24T19:40:48Z | |
| dc.description.abstract | Enantio- and diastereoselective hydrogenation of β-keto-γ-lactams with a ruthenium–BINAP catalyst, involving dynamic kinetic resolution, has been employed to provide a general, asymmetric approach to β-hydroxy-γ-lactams, a structural motif common to several bioactive compounds. Full conversion to the desired β-hydroxy-γ-lactams was achieved with high diastereoselectivity (up to >98% de) by addition of catalytic HCl and LiCl, while β-branching of the ketone substituent demonstrated a pronounced effect on the modest to excellent enantioselectivity (up to 97% ee) obtained. | en |
| dc.description.sponsorship | Enterprise Ireland (IP/2011/0097) | en |
| dc.description.status | Peer reviewed | en |
| dc.description.version | Accepted Version | en |
| dc.format.mimetype | application/pdf | en |
| dc.identifier.citation | Lynch, D., Deasy, R. E., Clarke, L.-A., Slattery, C. N., Khandavilli, U. B. R., Lawrence, S. E., Maguire, A. R., Magnus, N. A. & Moynihan, H. A. (2016) ‘Exploring the scope of asymmetric synthesis of β-Hydroxy-γ-lactams via Noyori-type reductions, Organic Letters, 18, 4978-4981. doi: 10.1021/acs.orglett.6b02416 | en |
| dc.identifier.doi | 10.1021/acs.orglett.6b02416 | |
| dc.identifier.endpage | 4981 | en |
| dc.identifier.issn | 1523-7060 | |
| dc.identifier.journaltitle | Organic letters | en |
| dc.identifier.startpage | 4978 | en |
| dc.identifier.uri | https://hdl.handle.net/10468/3333 | |
| dc.identifier.volume | 18 | en |
| dc.language.iso | en | en |
| dc.publisher | American Chemical Society | en |
| dc.rights | © 2016 American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://pubs.acs.org/doi/abs/10.1021/acs.orglett.6b02416 | en |
| dc.subject | Serotonin | en |
| dc.subject | Acid | en |
| dc.subject | Beta-branching | en |
| dc.title | Exploring the scope of asymmetric synthesis of β-Hydroxy-γ-lactams via Noyori-type reductions | en |
| dc.type | Article (peer-reviewed) | en |
