152615-80-0Relevant articles and documents
Four-component reactions toward fused heterocyclic rings
Airiau, Etienne,Girard, Nicolas,Mann, Andre,Salvadori, Jessica,Taddei, Maurizio
supporting information; experimental part, p. 5314 - 5317 (2010/02/28)
A multicomponent reaction between H2, CO, an unsaturated carboxylic acid derivative, and binucleophiles has been discovered. This process represents a combination of diversity-oriented synthesis and multicomponent reactions including amidation and hydroformylation, followed by nucleophilic addition to an N-acyliminium ion allowing the generation of six new bonds. Using π-nucleophiles, the sequence turns into a multicomponent Pictet-Spengler reaction.
Synthesis of Enantiopure trans-3,4-Disubstituted Piperidines. An Enantiodivergent Synthesis of (+)- And (-)-Paroxetine
Amat, Mercedes,Bosch, Joan,Hidalgo, Jose,Canto, Margalida,Perez, Maria,Llor, Nuria,Molins, Elies,Miravitlles, Carles,Orozco, Modesto,Luque, Javier
, p. 3074 - 3084 (2007/10/03)
Reaction of (R)-phenylglycinol with methyl 5-oxopentanoate gave either bicyclic lactam cis-1 (the kinetic product) or its isomer trans-1 (under equilibrating conditions) as the major products, which were converted to the corresponding (cis or trans) unsaturated lactams 4 and 5. On treatment with lithium alkyl (or aryl) cyanocuprates, these chiral building blocks undergo conjugate addition to give enantiopure trans-3,4-substituted 2-piperidone derivatives in high yield and stereoselectivity. The synthetic potential of this transformation is illustrated by the synthesis of (+)-femoxetine and the two enantiomers of the known antidepressant paroxetine.
Chiral precursors for the synthesis of enantiomerically pure piperidines. Total synthesis of (R)-(-)-coniine
Amat, Mercedes,Llor, Nuria,Bosch, Joan
, p. 2223 - 2226 (2007/10/02)
The preparation of chiral cis- and trans-oxazolopiperidones 1, 2, and 3 by alternative procedures and an efficient synthesis of the piperidine alkaloid (R)-(-)-coniine from trans-1 is reported.
