A convenient large-scale chiral synthesis of protected 2-substituted 4-oxo-piperidine derivatives

A convenient large-scale chiral synthesis of protected 2-substituted-4-oxo-piperidine derivatives is described. Hetero Diels–Alder reaction between trifluoroacetic acid–boron trifluoride activated (1-phenyl-ethylimino)acetic acid ethyl ester and 2-trimethylsilyloxy-1,3-butadiene gave rise to a mixtu...

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Bibliographic Details
Published inTetrahedron Vol. 58; no. 36; pp. 7339 - 7344
Main Authors Lau, Jesper F, Kruse Hansen, Thomas, Paul Kilburn, John, Frydenvang, Karla, Holsworth, Daniel D, Ge, Yu, Uyeda, Roy T, Judge, Luke M, Sune Andersen, Henrik
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 02.09.2002
Elsevier
Subjects
amino acids and derivatives
Chemistry
Chemistry, Organic
Diels–Alder reactions
Physical Sciences
piperidinones
Science & Technology
Diels–Alder reactions
piperidinones
amino acids and derivatives
Diels-Alder reactions
POTENT
PIPECOLIC ACID-DERIVATIVES
ASPARTIC ACID
4-OXOPIPECOLIC ACID
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Summary:A convenient large-scale chiral synthesis of protected 2-substituted-4-oxo-piperidine derivatives is described. Hetero Diels–Alder reaction between trifluoroacetic acid–boron trifluoride activated (1-phenyl-ethylimino)acetic acid ethyl ester and 2-trimethylsilyloxy-1,3-butadiene gave rise to a mixture of two diastereomers of 4-oxo-1-(1-phenyl-ethyl)-piperidine-2-carboxylic acid ethyl ester. Starting from ( S)-1-phenyl-ethylamine pure adduct can be obtained by crystallization of the diastereomeric mixture. Reduction of the ester group gave rise to the corresponding hydroxymethyl analogue, which was subjected to further functional group transformations to yield the desired protected 2-aminomethyl-4-oxo-piperidine derivative without any racemization being observed. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(02)00682-8