Synthesis of enantiopure functionalized pipecolic acids via amino acid derived N-acyliminium ions

Floris P.J.T. Rutjes; Johan J.N. Veerman; Wim J.N. Meester; Henk Hiemstra; Hans E. Schoemaker

doi:10.1002/(SICI)1099-0690(199905)1999:5<1127::AID-EJOC1127>3.0.CO;2-A

Synthesis of enantiopure functionalized pipecolic acids via amino acid derived N-acyliminium ions

Floris P.J.T. Rutjes, Johan J.N. Veerman, Wim J.N. Meester, Henk Hiemstra, Hans E. Schoemaker

Research output: Contribution to journal › Article › peer-review

60 Scopus citations

Abstract

The synthesis and enzymatic resolution of a novel vinylsilane-containing amino acid is described. Derivatization of this and other olefinic amino acids followed by subjection to standard N-acyliminium ion cyclization conditions provides the corresponding pipecolic acid derivatives with - in most cases - complete conservation of enantiopurity. In addition to studying the scope of this reaction, details of the N-acyliminium ion cyclization including an aza Cope equilibrium are highlighted.

Original language	English
Pages (from-to)	1127-1135
Number of pages	9
Journal	European Journal of Organic Chemistry
Issue number	5
DOIs	https://doi.org/10.1002/(SICI)1099-0690(199905)1999:5<1127::AID-EJOC1127>3.0.CO;2-A
State	Published - May 1999
Externally published	Yes

Keywords

Enzymatic resolution
N-Acyliminium ions
Non-natural amino acids
Pipecolic acid derivatives
Rearrangements

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10.1002/(SICI)1099-0690(199905)1999:5<1127::AID-EJOC1127>3.0.CO;2-A

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title = "Synthesis of enantiopure functionalized pipecolic acids via amino acid derived N-acyliminium ions",

abstract = "The synthesis and enzymatic resolution of a novel vinylsilane-containing amino acid is described. Derivatization of this and other olefinic amino acids followed by subjection to standard N-acyliminium ion cyclization conditions provides the corresponding pipecolic acid derivatives with - in most cases - complete conservation of enantiopurity. In addition to studying the scope of this reaction, details of the N-acyliminium ion cyclization including an aza Cope equilibrium are highlighted.",

keywords = "Enzymatic resolution, N-Acyliminium ions, Non-natural amino acids, Pipecolic acid derivatives, Rearrangements",

author = "Rutjes, \{Floris P.J.T.\} and Veerman, \{Johan J.N.\} and Meester, \{Wim J.N.\} and Henk Hiemstra and Schoemaker, \{Hans E.\}",

year = "1999",

month = may,

doi = "10.1002/(SICI)1099-0690(199905)1999:5<1127::AID-EJOC1127>3.0.CO;2-A",

language = "Ingl{\'e}s",

pages = "1127--1135",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "5",

}

TY - JOUR

T1 - Synthesis of enantiopure functionalized pipecolic acids via amino acid derived N-acyliminium ions

AU - Rutjes, Floris P.J.T.

AU - Veerman, Johan J.N.

AU - Meester, Wim J.N.

AU - Hiemstra, Henk

AU - Schoemaker, Hans E.

PY - 1999/5

Y1 - 1999/5

N2 - The synthesis and enzymatic resolution of a novel vinylsilane-containing amino acid is described. Derivatization of this and other olefinic amino acids followed by subjection to standard N-acyliminium ion cyclization conditions provides the corresponding pipecolic acid derivatives with - in most cases - complete conservation of enantiopurity. In addition to studying the scope of this reaction, details of the N-acyliminium ion cyclization including an aza Cope equilibrium are highlighted.

AB - The synthesis and enzymatic resolution of a novel vinylsilane-containing amino acid is described. Derivatization of this and other olefinic amino acids followed by subjection to standard N-acyliminium ion cyclization conditions provides the corresponding pipecolic acid derivatives with - in most cases - complete conservation of enantiopurity. In addition to studying the scope of this reaction, details of the N-acyliminium ion cyclization including an aza Cope equilibrium are highlighted.

KW - Enzymatic resolution

KW - N-Acyliminium ions

KW - Non-natural amino acids

KW - Pipecolic acid derivatives

KW - Rearrangements

UR - https://www.scopus.com/pages/publications/0032783850

U2 - 10.1002/(SICI)1099-0690(199905)1999:5<1127::AID-EJOC1127>3.0.CO;2-A

DO - 10.1002/(SICI)1099-0690(199905)1999:5<1127::AID-EJOC1127>3.0.CO;2-A

M3 - Artículo

AN - SCOPUS:0032783850

SN - 1434-193X

SP - 1127

EP - 1135

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 5

ER -

Synthesis of enantiopure functionalized pipecolic acids via amino acid derived N-acyliminium ions

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