267011-73-4Relevant articles and documents
Regioselective synthesis of substituted piperidine-2,4-diones and their derivatives via Dieckmann cyclisations
Marson, Charles M.,Yau, Kin Cheung
, p. 7459 - 7469 (2015/08/24)
Abstract A flexible route to piperidine-2,4-diones variously substituted at the 6-, 5,6- and 2,6-positions, both with and without 1-substitution, is described; no N-protective group is required. A related regioselective Dieckmann cyclisation is also described that uses Davies' α-methylbenzylamine auxiliary and affords 6-substituted piperidine-2,4-diones enantioselectively.
Intramolecular Mannich reaction in the asymmetric synthesis of polysubstituted piperidines: concise synthesis of the dendrobate alkaloid (+)-241D and its C-4 epimer.
Davis,Chao,Rao
, p. 3169 - 3171 (2007/10/03)
[reaction: see text] The intramolecular Mannich reaction of delta-amino beta-keto esters with aldehydes and ketones is a new methodology for the synthesis of polysubstituted piperidines and is illustrated by the concise asymmetric synthesis of the dendrob
Addition of dienolates to sulfinimines. Stereoselective synthesis of dihydropyridones
Kaw, Robert
, p. 8385 - 8390 (2007/10/03)
The vinylogous Mannich reaction of sulfinimines with dienolates was investigated. Lithium and trimethylsilyl enolates of ethyl 3-ethoxycrotonate reacted with enantiopure 10-isobornylsulfinimines to give derivatives of δ-aminoacids which were cyclised to 6-aryl substituted derivatives of 2(1H)-pyridinones. 6-Aryl substituted 2,4-piperidinediones with either (S) or (R) configuration were analogously obtained using lithium and TMS enolates of 2,2,6-trimethyl-1,3-dioxin-4-one.