326477-43-4Relevant academic research and scientific papers
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.
Asymmetric synthesis of alkaloids using polyfunctionalized chiral building blocks
Davis, Franklin A.,Chao, Bin,Andemichael, Yemane W.,Mohanty, Pradyumna K.,Fang, Tianan,Burns, David M.,Rao, Ashwin,Szewczyk, Joanna M.
, p. 486 - 492 (2007/10/03)
Enantiopure N-sulfinyl-δ-amino-β-ketoesters and isoquinolones, prepared from sulfinimines (N-sulfinyl imines) are a new class of polyfunctionalized chiral building blocks. These building blocks provide easy access to enantiomerically pure, functionalized piperidines and tetrahydroisoquinolines with a minimum of chemical manipulation and protecting-group chemistry.
Asymmetric synthesis of the four stereoisomers of 4-hydroxypipecolic acid
Davis,Fang,Chao,Burns
, p. 2106 - 2112 (2007/10/03)
The asymmetric synthesis of all four stereoisomers of 4-hydroxypipecolic acid (1) from the polyfunctionalized chiral building blocks δ-amino β-keto esters (S(S),R)-(+)-5 or (R(S),S)-(-)-5 is described. Key steps in the synthesis are the stereoselective reductions of b-phenylpiperidine-2,4-dione (6) and N-sulfinyl δ-amino β-keto esters 5 to cis 4-hydroxy 2-piperidinone 7 and syn-δ-amino β-hydroxy ester 9, respectively. The only protecting/deprotecting group chemistry required is related to the oxidation step.
