Tetrahedron

Enantioselective synthesis of β-amino acids. Part 11: Diastereoselective alkylation of chiral derivatives of β-aminopropionic acid containing the α-phenethyl group

…, H López-Ruiz, G Reyes-Rangel, E Juaristi

Index: Gutierrez-Garcia, Victor Manuel; Lopez-Ruiz, Heraclio; Reyes-Rangel, Gloria; Juaristi, Eusebio Tetrahedron, 2001 , vol. 57, # 30 p. 6487 - 6496

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Citation Number: 35

Abstract

Several novel, chiral derivatives of β-aminopropionic acid were studied as potentially useful precursors of enantiopure α-substituted-β-amino acids. In particular, the diastereoselectivity of alkylation of (R, R)-2-Li enolate showed substantial stereoinduction by the bis [α- phenylethyl] amide auxiliary, leading to 80% ds in the methylation reaction. No appreciable effect upon diastereoselectivity was observed by the presence of additives (LiCl, HMPA, ...