Exploring the scope of asymmetric synthesis of β-Hydroxy-γ-lactams via Noyori-type reductions
| Data(s) |
01/12/2016
01/12/2016
22/09/2016
24/11/2016
|
|---|---|
| Resumo |
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. |
| Formato |
application/pdf |
| Identificador |
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 18 4978 4981 1523-7060 http://hdl.handle.net/10468/3333 10.1021/acs.orglett.6b02416 Organic letters |
| Idioma(s) |
en |
| Publicador |
American Chemical Society |
| Direitos |
© 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 |
| Palavras-Chave | #Serotonin #Acid #Beta-branching |
| Tipo |
Article (peer-reviewed) |
