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

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

In: Tetrahedron, Vol. 58, No. 36, 02.09.2002, p. 7339-7344.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Lau, JF, Kruse Hansen, T, Paul Kilburn, J, Frydenvang, K, Holsworth, DD, Ge, Y, Uyeda, RT, Judge, LM & Sune Andersen, H 2002, 'A convenient large-scale chiral synthesis of protected 2-substituted 4-oxo-piperidine derivatives', Tetrahedron, vol. 58, no. 36, pp. 7339-7344. https://doi.org/10.1016/S0040-4020(02)00682-8

APA

Lau, J. F., Kruse Hansen, T., Paul Kilburn, J., Frydenvang, K., Holsworth, D. D., Ge, Y., Uyeda, R. T., Judge, L. M., & Sune Andersen, H. (2002). A convenient large-scale chiral synthesis of protected 2-substituted 4-oxo-piperidine derivatives. Tetrahedron, 58(36), 7339-7344. https://doi.org/10.1016/S0040-4020(02)00682-8

Vancouver

Lau JF, Kruse Hansen T, Paul Kilburn J, Frydenvang K, Holsworth DD, Ge Y et al. A convenient large-scale chiral synthesis of protected 2-substituted 4-oxo-piperidine derivatives. Tetrahedron. 2002 Sep 2;58(36):7339-7344. https://doi.org/10.1016/S0040-4020(02)00682-8

Author

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. / A convenient large-scale chiral synthesis of protected 2-substituted 4-oxo-piperidine derivatives. In: Tetrahedron. 2002 ; Vol. 58, No. 36. pp. 7339-7344.

Bibtex

@article{5c231e50ccd447d080d35ff993f6fe80,
title = "A convenient large-scale chiral synthesis of protected 2-substituted 4-oxo-piperidine derivatives",
abstract = "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.",
keywords = "Amino acids and derivatives, Diels-Alder reactions, Piperidinones",
author = "Lau, {Jesper F.} and {Kruse Hansen}, Thomas and {Paul Kilburn}, John and Karla Frydenvang and Holsworth, {Daniel D.} and Yu Ge and Uyeda, {Roy T.} and Judge, {Luke M.} and {Sune Andersen}, Henrik",
year = "2002",
month = sep,
day = "2",
doi = "10.1016/S0040-4020(02)00682-8",
language = "English",
volume = "58",
pages = "7339--7344",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Pergamon Press",
number = "36",

}

RIS

TY - JOUR

T1 - A convenient large-scale chiral synthesis of protected 2-substituted 4-oxo-piperidine derivatives

AU - Lau, Jesper F.

AU - Kruse Hansen, Thomas

AU - Paul Kilburn, John

AU - Frydenvang, Karla

AU - Holsworth, Daniel D.

AU - Ge, Yu

AU - Uyeda, Roy T.

AU - Judge, Luke M.

AU - Sune Andersen, Henrik

PY - 2002/9/2

Y1 - 2002/9/2

N2 - 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.

AB - 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.

KW - Amino acids and derivatives

KW - Diels-Alder reactions

KW - Piperidinones

UR - http://www.scopus.com/inward/record.url?scp=0037008913&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(02)00682-8

DO - 10.1016/S0040-4020(02)00682-8

M3 - Journal article

AN - SCOPUS:0037008913

VL - 58

SP - 7339

EP - 7344

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 36

ER -

ID: 382746837