152555-02-7Relevant articles and documents
Synthesis and reactivity of endocyclic α-cyanoenamines in the phenyloxazolopiperidine series
Lallemand,Francois,Laimer,Kunesch,Husson
, p. 3231 - 3239 (2001)
Using the capto-dative character of piperidine building block 1, the diastereomeric α-cyanoenamines 2a and 2b accompanied by dimer 5 were prepared through a SET pathway in a one-step procedure. Adjustment of the reaction conditions afforded either 2a or 2
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.
A general approach to aza-heterocycles by means of domino sequences driven by hydroformylation
Airiau, Etienne,Spangenberg, Thomas,Girard, Nicolas,Schoenfelder, Angele,Salvadori, Jessica,Taddei, Maurizio,Mann, Andre
experimental part, p. 10938 - 10948 (2009/11/30)
The development of hydroformylative domino reactions of easily accessible vinyl acetamides is described. Extremely regioselective hydroformylation of terminal double bounds provides a transient N-acyliminium that can be trapped by various nucleophiles to give several aza-heterocylic scaffolds in a diastereoselective manner.
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.
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.
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
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.
Asymmetric Synthesis of Spiro 2-Pyrrolidin-5-ones and 2-Piperidin-6-ones
Bahajaj, Abood A.,Bailey, Patrick D.,Moore, Madeleine H.,Morgan, Keith M.,Vernon, John M.
, p. 2511 - 2512 (2007/10/02)
Bicyclic lactams 14-17 are isomerised on treatment with aluminium trichloride in 1,2-dichloroethane to give spiro lactams in high yield and > 3:1 diastereoselectivity; from the structures of 19a and 22b determined by X-ray crystallography, it follows that
A NEW POTENTIAL ACYL IMINIUM ION FOR THE ASYMMETIRIC SYNTHESIS OF PIPERIDINE DERIVATIVES
Royer, Jacques,Husson, Henri-Phillipe
, p. 1493 - 1496 (2007/10/02)
Epimeric oxazolopiperidones (1a) and (1b) were prepared independently, both from R-(-)-phenylglycinol as starting material.They represent chiral potential iminium ions.
