Regioselective synthesis of substituted piperidine-2,4-diones and their derivatives via Dieckmann cyclisations》.pdf

Tetrahedron 71 (2015) 7459e7469 Contents lists available at ScienceDirect Tetrahedron journal homepage: www.elsevier.c om/locate/tet Regioselective synthesis of substituted piperidine-2,4-diones and their derivatives via Dieckmann cyclisations Charles M. Marson *, Kin Cheung Yau Department of Chemistry, University College London, Christopher Ingold Laboratories, 20 Gordon Street, London WC1H OAJ, UK a r t i c l e i n f o a b s t r a c t Article history: A flexible route to piperidine-2,4-diones variously substituted at the 6-, 5,6- and 2,6-positions, both with Received 21 May 2015 and without 1-substitution, is described; no N-protective group is required. A related regioselective Received in revised form 9 June 2015 Dieckmann cyclisation is also described that uses Davies’ a-methylbenzylamine auxiliary and affords 6- Accepted 12 June 2015 substituted piperidine-2,4-diones enantioselectively. Available online 19 June 2015 2015 Elsevier Ltd. All rights reserved. Keywords: Dieckmann cyclisation Piperidine-2,4-diones Regioselective synthesis Enantioselective synthesis 1. Introduction 2. Results and discussion The piperidine ring, a privileged scaffold in pharmaceutically It was desired to investigate the scope of Dieckmann cyclisations active compounds,1 is exemplified in the numerous pip