156873-53-9Relevant academic research and scientific papers
Stereoselective α-amidoalkylation reactions of phenylglycinol-derived bicyclic lactams
Amat, Mercedes,Escolano, Carmen,Llor, Nuria,Huguet, Marta,Perez, Maria,Bosch, Joan
, p. 1679 - 1683 (2003)
The stereochemical outcome of α-amidoalkylation reactions from the chiral non-racemic bicyclic lactams trans-1 and cis-1 using indole, allyltrimethylsilane, higher order organocuprates, TMSCN, and Grignard reagents is discussed.
Enantioselective synthesis of piperidine, indolizidine, and quinolizidine alkaloids from a phenylglycinol-derived δ-lactam
Amat, Mercedes,Llor, Nuria,Hidalgo, Jose,Escolano, Carmen,Bosch, Joan
, p. 1919 - 1928 (2007/10/03)
Starting from a common lactam, (3R,8aS)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (1), or its enantiomer, the enantioselective synthesis of 2-alkylpiperidines and cis- and trans-2,6-dialkylpiperidines is reported. The potential of this approach is illustrated by the synthesis of the piperidine alkaloids (R)-coniine, (2R,6S)-dihydropinidine, (2R,6R)-lupetidine, and (2R,6R)-solenopsin A, the indolizidine alkaloids (5R,8aR)-indolizidine 167B and (3R,5S,8aS)-monomorine I, and the nonnatural base (4R,9aS)-4-methylquinolizidine.
New methodology for the synthesis of enantiopure (3R,2aR)-(-)-3-phenyl-hexahydro-oxazolo[3,2-a]-pyridin-5-one: A synthesis of (S)-(+)-coniine
Teran,Gnecco,Galindo,Juarez,Bernes,Enriquez
, p. 357 - 360 (2007/10/03)
A new and efficient methodology for the enantiopure synthesis of (3R,2aR)-(-)-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-one 3 starting from (1′R)-(-)-1-(2′-hydroxy-1′-phenyl-ethyl)-(1H)-pyridin-2-one 1 is described. In addition, the enantiospecific synthesis of (S)-(+)-coniine hydrochloride 6 in good yield from 3 is reported.
