653589-22-1Relevant academic research and scientific papers
A new method of synthesis of 6-substituted piperidine-2,4-diones from homoallylamines
Kuznetsov, Nikolai Yu.,Maleev, Victor I.,Khrustalev, Victor N.,Mkrtchyan, Anna F.,Godovikov, Ivan A.,Strelkova, Tatyana V.,Bubnov, Yuri N.
experimental part, p. 334 - 344 (2012/02/16)
Mono- and dihomoallylamines serve as convenient precursors for the preparation of 6-substituted piperidine-2,4-diones. This transformation is based, on the one hand, on a simple and well-known halocyclocarbamation reaction proceeding by the addition of a
Synthesis of Enantiopure 4-Hydroxypipecolate and 4-Hydroxylysine Derivatives from a Common 4,6-Dioxopiperidinecarboxylate Precursor
Marin,Didierjean,Aubry,Casimir,Briand,Guichard
, p. 130 - 141 (2007/10/03)
tert-Butyl 2-substituted 4,6-dioxo-1-piperidinecarboxylates 4 have been prepared in good yield starting from Boc-Asp-OtBu and other β-amino acids. By analogy with chiral tetramic acids, their reduction by NaBH4 in CH2Cl2/AcOH afforded the corresponding cis-4-hydroxy δ-lactams in good yield and stereoselectivity (68-98% de). In the absence of the A(1,3) strain (reduction of 6-substituted 2,4-dioxo-1-piperidines 7), the cis-4-hydroxy isomer was still obtained as the major product but the de values were consistently lower. 4-Hydroxy-6-oxo- 1,2-piperidinedicarboxylate 2a, readily accessible from Boc-Asp-OtBu (three steps, 63% overall yield), has proven to be an excellent building block for the synthesis of cis- and trans-4-hydroxypipecolates 17 and 24 (52 and 36% overall yield, respectively) and for the synthesis of a protected 4-hydroxylysine derivative 29 (41% overall yield).
