Enantioselective synthesis of (+)-(2 S,4 S,6 S)-1-ethoxycarbonyl-6-hydroxymethyl-4-methylpipecolate

Graphic The enantioselective synthesis of (+)-(2 S,4 S,6 S)-1-ethoxycarbonyl-6-hydroxymethyl-4-methylpipecolamide 16 is described. The absolute configuration of stereocenters introduced in (+)- 16 was assigned on the basis of 1H NMR data. The results extend the chirality transfer with complete contr...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 15; no. 4; pp. 693 - 697
Main Authors Acherki, Hassan, Alvarez-Ibarra, Carlos, Guzmán-Fernández, Susana, Quiroga-Feijóo, Marı́a L.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 23.02.2004
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
ACYLIMINIUM ION
CARBON
DIASTEREOSELECTIVE SYNTHESIS
ALPHA-AMIDOALKYLATION
2R,5S-5-HYDROXYPIPECOLIC ACID
INTERMEDIATE
LACTAMS
ALDEHYDES
PIPECOLIC ACIDS
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Summary:Graphic The enantioselective synthesis of (+)-(2 S,4 S,6 S)-1-ethoxycarbonyl-6-hydroxymethyl-4-methylpipecolamide 16 is described. The absolute configuration of stereocenters introduced in (+)- 16 was assigned on the basis of 1H NMR data. The results extend the chirality transfer with complete control of stereoselectivity from the sulfinyl group to the 4-position and, hence, to the 6- and 2-positions of the piperidine ring via asymmetric induction.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2003.11.035