Exploring the scope of asymmetric synthesis of β-Hydroxy-γ-lactams via Noyori-type reductions
Lynch, Denis; Deasy, Rebecca E.; Clarke, Leslie-Ann; Slattery, Catherine N.; Khandavilli, Udaya Bhaskara Rao; Lawrence, Simon E.; Maguire, Anita R.; Magnus, Nicholas A.; Moynihan, Humphrey A.
Date:
2016-09-22
Copyright:
© 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
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
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.
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