Diastereoselective synthesis of chiral methyl 2-piperidin-2-ylpropanoates

Heterocycles

Volumn 71, Issue 2, 2007, Pages 437-444

  Pereira, Jennifer ^a   Calvet Vitale, Sandrine ^a   Fargeau Bellassoued, Marie Claude ^a   Mouries Mansuy, Virginie ^a   Vanucci Bacqué, Corinne ^a   Lhommet, Gérard ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34547134975     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-06-10938     Document Type: Article

References (35)

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26. Determined by GC analysis.
27. In ref. 11, the experimental details were not described and the obtained alkylated piperidine β-amino esters were only partially characterized. Moreover, the optical rotation values have been mistakenly reported as positive, and must be read as negative.
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30. A similar result was obtained for pyrrolidine homologue alkylation: see ref. 9.
31. The procedure was improved by the successful purification of 1 by a very short column filtration on silica gel (AcOEt) with a similar yield (87%).
32. 2 as the catalyst.
33. 10
34. The reaction was also conducted starting from enantiopure piperidine (4a) to afford pure compound (5a).
35. 2/C catalyzed hydrogenation (0.15 equiv in weight) of 1 was also carried out with a similar diastereoselectivity, provided that two additions of the catalyst were performed successively (0.05 equiv for 12h and 0.10 equiv for 3h).