A new synthesis of β-amino acids by use of ketene diethyl acetal as enolate equivalent

[Display omitted] Reaction of phenylsulfonyl formamides, readily available in a single step from an aromatic aldehyde and sodium phenylsulfinate, with ketene diethyl acetal under basic conditions gives N-formyl β-amino acid esters in good yield, which can be kinetically resolved with a lipase.

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Bibliographic Details
Published inTetrahedron letters Vol. 46; no. 11; pp. 1819 - 1821
Main Authors Rossen, Kai, Jakubec, Pavol, Kiesel, Michael, Janik, Matthias
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 14.03.2005
Elsevier
Subjects
Acetate enolate
Acyl imine
Chemistry
Chemistry, Organic
Enzymic kinetic resolution
Ketene diethylacetal
Physical Sciences
Science & Technology
β-Amino acid
Acyl imine
Enzymic kinetic resolution
Acetate enolate
β-Amino acid
Ketene diethylacetal
ketene diethylacetal
beta-amino acid
ALDEHYDES
acetate enolate
enzymic kinetic resolution
DERIVATIVES
acyl imine
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Summary:[Display omitted] Reaction of phenylsulfonyl formamides, readily available in a single step from an aromatic aldehyde and sodium phenylsulfinate, with ketene diethyl acetal under basic conditions gives N-formyl β-amino acid esters in good yield, which can be kinetically resolved with a lipase.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2005.01.114