159173-92-9Relevant academic research and scientific papers
Access to 2,6-disubstituted piperidines: Control of the diastereoselectivity, scope, and limitations. applications to the stereoselective synthesis of (-)-solenopsine A and alkaloid (+)-241D
Abrunhosa-Thomas, Isabelle,Plas, Aurelie,Vogrig, Alexandre,Kandepedu, Nishanth,Chalard, Pierre,Troin, Yves
, p. 2511 - 2526 (2013/04/24)
Scope and limitations in the diastereoselective preparation of 2,6-cis or 2,6-trans disubstituted piperidines are described, through intramolecular reaction of chiral β′-carbamate-α,β-unsaturated ketone. This methodology has been applied to the total synthesis of a few well chosen examples, such as (-)-solenopsine A and alkaloid (+)-241D.
Stereoselective synthesis and in vivo evaluation of the analgesic activity of polysubstituted bispidines
Plas, Aurelie,Troin, Yves,Chalard, Pierre,Marchand, Fabien,Eschalier, Alain
supporting information, p. 6070 - 6079,10 (2020/09/02)
Hetero-Michael addition on a chiral β'-amino α,β- unsaturated ketone gave, after some structural modifications, β,β'-diamino ketals. Mannich-type reactions of these diamines with an aldehyde led, with high diastereoselectivity, to trisubstituted piperidines. Another highly stereoselective Mannich cyclization, with an N-acyliminium ion generated in situ from the corresponding imide, allowed the preparation of original polycyclic bispidine derivatives. The antinociceptive effect of the three compounds prepared was evaluated in vivo by using the writhing test. If the biological results for the analgesic properties were disappointing, compared with the bispidine HZ2, which has a high affinity for opioid receptors, the modularity of the approach offered the possibility of introducing many substituents for new applications, which was promising because the bispidine core has been described to have many different activities. Total stereoselective synthesis of bispidine derivatives is achieved by using as two successive Mannich reactions key steps. This process constitutes a powerful approach toward the preparation of a polycyclic bispidine backbone with high enantioselectivity.
Homochiral lithium amides for the asymmetric synthesis of β-amino acids
Davies, Stephen G.,Garrido, Narciso M.,Kruchinin, Dennis,Ichihara, Osamu,Kotchie, Luke J.,Price, Paul D.,Mortimer, Anne J. Price,Russell, Angela J.,Smith, Andrew D.
, p. 1793 - 1811 (2007/10/03)
Secondary homochiral lithium amides derived from α-methylbenzylamine undergo highly diastereoselective conjugate additions to a range of α,β-unsaturated esters. The corresponding β-amino acids are readily liberated by successive N-debenzylation and ester hydrolysis, furnishing (R)-β-amino butyric acid, (R)-β-amino pentanoic acid, (S)-β-leucine, (R)-β-amino octanoic acid, (S)-β-phenylalanine, (S)-β-tyrosine methyl ether, (S)-β-tyrosine hydrochloride and (S)-β-(2-methoxyphenyl)-β-amino propanoic acid in high yields and high ee. The application of this procedure to the synthesis of the natural products (R)-β-DOPA and (R)-β-lysine is demonstrated. The development of a simplified one-pot reaction protocol applicable to the multi-gram scale synthesis of homochiral β-amino esters is also delineated.
A facile enantioselective synthesis of 2-(2-aminoethyl)allylsilanes, new synthons for piperidine synthesis
Monfray, Jérémy,Gelas-Mialhe, Yvonne,Gramain, Jean-Claude,Remuson, Roland
, p. 5785 - 5787 (2007/10/03)
The synthesis of chiral (2-substituted-2-aminoethyl)allylsilanes by cerium mediated trimethylsilylmethylmagnesium chloride addition to the ester group of non racemic chiral β-aminoesters is described.
Asymmetric synthesis of anti-α-alkyl-β-amino carboxamides
Davies, Stephen G.,Edwards, Alison J.,Walters, Iain A. S.
, p. 175 - 183 (2007/10/02)
The alkylation reactions of enolates derived from the highly diastereoselective conjugate additions of lithium (R)-N-benzyl-N-α-methylbenzylamide (R)-1 to N,N-dimethyl crotonamide 2 and N,N-dimethyl cinnamide 3 have been investigated.The alkylations of en
Asymmetric Synthesis of anti-α-Alkyl-β-amino Acids
Davies, Stephen G.,Walters, Iain A. S.
, p. 1129 - 1140 (2007/10/02)
An investigation into the asymmetric induction accompanying alkylations of enolates derived from the highly diastereoselective conjugate addition of lithium (R)-N-benzyl-N-α-methylbenzylamide (R)-1 to crotonate and cinnamate esters has been performed.The
