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Closed Access item First asymmetric synthesis of an acyclic β,β-dialkylated-γ-aminobutyric acid

Authors:Aguirre, Daniel
Cativiela, Carlos
Díaz-de-Villegas, María D.
Gálvez, José A.
Keywords:γ-Amino acids, Asymmetric synthesis, Diastereoselective alkylation
Issue Date:21-Aug-2006
Publisher:Elsevier
Citation:Tetrahedron 62(34): 8142-8146 (2006)
Abstract:Enantiomerically pure (R)-γ-amino-β-benzyl-β-methylbutyric acid, an acyclic β,β-dialkyl GABA derivative, is efficiently synthesised from (1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl 2-cyanopropanoate by a sequence based on benzylation, Arndt–Eistert homologation and nitrile reduction. Benzylation of (1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl 2-cyanopropanoate using potassium carbonate under not strictly anhydrous conditions occurs diastereoselectively to afford (1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl (S)-2-cyano-2-methyl-3-phenylpropanoate, the key chiral intermediate from which the desired γ-amino acid is obtained in five steps in 65% overall yield.
Description:5 pages, 2 schemes, 1 figure.
Publisher version (URL):http://dx.doi.org/10.1016/j.tet.2006.06.021
URI:http://hdl.handle.net/10261/19047
ISSN:0040-4020
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