Catalytic enantioselective 5-hydroxyisoxazolidine synthesis: An asymmetric entry to β-amino acids

Ismail Ibrahem; Ramon Rios; Jan Vesely; Gui Ling Zhao; Armando Córdova

doi:10.1055/s-2007-990935

Catalytic enantioselective 5-hydroxyisoxazolidine synthesis: An asymmetric entry to β-amino acids

Ismail Ibrahem, Ramon Rios, Jan Vesely, Gui Ling Zhao, Armando Córdova

Chemistry

Arrhenius Laboratory

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

29 Scopus citations

Abstract

The highly chemo- and enantioselective organocatalytic tandem reaction between N-carbamate-protected hydroxylamines and α,β-unsaturated aldehydes is presented. The reaction represents a unique entry for the asymmetric synthesis of 5-hydroxyisoxazolidines, oxazolidin-5-ones or γ-hydroxyamino alcohols in high yields and 90-99% ee. A procedure for the conversion of the oxazolidin-5-ones into the corresponding β-amino acids is also described.

Original language	British English
Pages (from-to)	1153-1157
Number of pages	5
Journal	Synthesis
Issue number	7
DOIs	https://doi.org/10.1055/s-2007-990935
State	Published - 1 Apr 2008

Keywords

β-amino acid synthesis
Amination reactions
Asymmetric catalysis
Isoxazolidines
Organocatalysis

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10.1055/s-2007-990935

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title = "Catalytic enantioselective 5-hydroxyisoxazolidine synthesis: An asymmetric entry to β-amino acids",

abstract = "The highly chemo- and enantioselective organocatalytic tandem reaction between N-carbamate-protected hydroxylamines and α,β-unsaturated aldehydes is presented. The reaction represents a unique entry for the asymmetric synthesis of 5-hydroxyisoxazolidines, oxazolidin-5-ones or γ-hydroxyamino alcohols in high yields and 90-99% ee. A procedure for the conversion of the oxazolidin-5-ones into the corresponding β-amino acids is also described.",

keywords = "β-amino acid synthesis, Amination reactions, Asymmetric catalysis, Isoxazolidines, Organocatalysis",

author = "Ismail Ibrahem and Ramon Rios and Jan Vesely and Zhao, {Gui Ling} and Armando C{\'o}rdova",

year = "2008",

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doi = "10.1055/s-2007-990935",

language = "British English",

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TY - JOUR

T1 - Catalytic enantioselective 5-hydroxyisoxazolidine synthesis

T2 - An asymmetric entry to β-amino acids

AU - Ibrahem, Ismail

AU - Rios, Ramon

AU - Vesely, Jan

AU - Zhao, Gui Ling

AU - Córdova, Armando

PY - 2008/4/1

Y1 - 2008/4/1

N2 - The highly chemo- and enantioselective organocatalytic tandem reaction between N-carbamate-protected hydroxylamines and α,β-unsaturated aldehydes is presented. The reaction represents a unique entry for the asymmetric synthesis of 5-hydroxyisoxazolidines, oxazolidin-5-ones or γ-hydroxyamino alcohols in high yields and 90-99% ee. A procedure for the conversion of the oxazolidin-5-ones into the corresponding β-amino acids is also described.

AB - The highly chemo- and enantioselective organocatalytic tandem reaction between N-carbamate-protected hydroxylamines and α,β-unsaturated aldehydes is presented. The reaction represents a unique entry for the asymmetric synthesis of 5-hydroxyisoxazolidines, oxazolidin-5-ones or γ-hydroxyamino alcohols in high yields and 90-99% ee. A procedure for the conversion of the oxazolidin-5-ones into the corresponding β-amino acids is also described.

KW - β-amino acid synthesis

KW - Amination reactions

KW - Asymmetric catalysis

KW - Isoxazolidines

KW - Organocatalysis

UR - http://www.scopus.com/inward/record.url?scp=42049098788&partnerID=8YFLogxK

U2 - 10.1055/s-2007-990935

DO - 10.1055/s-2007-990935

M3 - Article

AN - SCOPUS:42049098788

SN - 0039-7881

SP - 1153

EP - 1157

JO - Synthesis

JF - Synthesis

IS - 7

ER -

Catalytic enantioselective 5-hydroxyisoxazolidine synthesis: An asymmetric entry to β-amino acids

Abstract

Keywords

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