185330-37-4Relevant academic research and scientific papers
Enantioselective synthesis of 3,3-disubstituted piperidine derivatives by enolate dialkylation of phenylglycinol-derived oxazolopiperidone lactams
Amat, Mercedes,Lozano, Oscar,Escolano, Carmen,Molins, Elies,Bosch, Joan
, p. 4431 - 4439 (2008/02/05)
(Chemical Equation Presented) The stereochemical outcome of the enolate dialkylation of simple phenylglycinol-derived oxazolopiperidone lactams is studied. High stereoselectivities in the generation of the quaternary stereocenter are obtained by the appropriate choice of both the configuration of the starting lactam and the order of introduction of the substituents. The usefulness of the methodology is illustrated by the conversion of some of the dialkylated lactams into known synthetic precursors of alkaloids and by the total synthesis of (-)-quebrachamine.
Alkylation of phenylglycinol-derived oxazolopiperidone lactams. Enantioselective synthesis of β-substituted piperidines
Amat, Mercedes,Escolano, Carmen,Lozano, Oscar,Gomez-Esque, Arantxa,Griera, Rosa,Molins, Elies,Bosch, Joan
, p. 3804 - 3815 (2007/10/03)
The stereochemical outcome of the alkylation of a variety of phenylglycinol-derived oxazolopiperidone lactams is studied. The influence of the configuration of the C-8a stereocenter and the effect of the substituents at the C-8 and C-8a positions on the s
Enantioselective syntheses of the indole alkaloid (+)-R-decarbomethoxytetrahydrosecodine and its enantiomer
Amat, Mercedes,Pshenichnyi, Grigorii,Bosch, Joan,Molins, Elies,Miravitlles, Carles
, p. 3091 - 3094 (2007/10/03)
The alkaloid (+)-R-decarbomethoxytetrahydrosecodine (+)-1 has been synthesized by alkylation of (R)-3-ethylpiperidine with 3-(2-bromoethyl)-2-ethylindole (7). The required enantiopure piperidine was prepared by alkylation of the chiral non-racemic oxazolo
