Aminolysis of resin-bound N-nosylaziridine-2-carboxylic acids

Christian A Olsen; Caspar Christensen; Birgitte Nielsen; Mohamed M Farah; Farah M Mohamed; Matthias Witt; Rasmus P Clausen; Jesper L Kristensen; Henrik Franzyk; Jerzy W Jaroszewski

doi:10.1021/ol061304e

Aminolysis of resin-bound N-nosylaziridine-2-carboxylic acids

Christian A Olsen, Caspar Christensen, Birgitte Nielsen, Mohamed M Farah, Farah M Mohamed, Matthias Witt, Rasmus P Clausen, Jesper L Kristensen, Henrik Franzyk, Jerzy W Jaroszewski

22 Citations (Scopus)

Abstract

[Structure: see text] Solid-phase synthesis is a rapidly developing area of organic chemistry, of particular importance for medicinal chemistry and chemical biology. Aziridines have previously only rarely been applied in solid-phase synthesis. In the present work, aminolysis of resin-bound, spring-loaded N-nitrobenzenesulfonyl-activated aziridine-2-carboxylic acids has been optimized and employed in the synthesis of a number of open-chain and heterocyclic scaffolds, including enantiopure products.

Original language	English
Journal	Organic Letters
Volume	8
Issue number	15
Pages (from-to)	3371-4
Number of pages	4
ISSN	1523-7060
DOIs	https://doi.org/10.1021/ol061304e
Publication status	Published - 2006

Keywords

Amino Alcohols
Aziridines
Carboxylic Acids
Heterocyclic Compounds
Molecular Structure
Stereoisomerism

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10.1021/ol061304e

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title = "Aminolysis of resin-bound N-nosylaziridine-2-carboxylic acids",

abstract = "[Structure: see text] Solid-phase synthesis is a rapidly developing area of organic chemistry, of particular importance for medicinal chemistry and chemical biology. Aziridines have previously only rarely been applied in solid-phase synthesis. In the present work, aminolysis of resin-bound, spring-loaded N-nitrobenzenesulfonyl-activated aziridine-2-carboxylic acids has been optimized and employed in the synthesis of a number of open-chain and heterocyclic scaffolds, including enantiopure products.",

keywords = "Amino Alcohols, Aziridines, Carboxylic Acids, Heterocyclic Compounds, Molecular Structure, Stereoisomerism",

author = "Olsen, {Christian A} and Caspar Christensen and Birgitte Nielsen and Farah, {Mohamed M} and Mohamed, {Farah M} and Matthias Witt and Clausen, {Rasmus P} and Kristensen, {Jesper L} and Henrik Franzyk and Jaroszewski, {Jerzy W}",

year = "2006",

doi = "10.1021/ol061304e",

language = "English",

volume = "8",

pages = "3371--4",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "15",

}

TY - JOUR

T1 - Aminolysis of resin-bound N-nosylaziridine-2-carboxylic acids

AU - Olsen, Christian A

AU - Christensen, Caspar

AU - Nielsen, Birgitte

AU - Farah, Mohamed M

AU - Mohamed, Farah M

AU - Witt, Matthias

AU - Clausen, Rasmus P

AU - Kristensen, Jesper L

AU - Franzyk, Henrik

AU - Jaroszewski, Jerzy W

PY - 2006

Y1 - 2006

N2 - [Structure: see text] Solid-phase synthesis is a rapidly developing area of organic chemistry, of particular importance for medicinal chemistry and chemical biology. Aziridines have previously only rarely been applied in solid-phase synthesis. In the present work, aminolysis of resin-bound, spring-loaded N-nitrobenzenesulfonyl-activated aziridine-2-carboxylic acids has been optimized and employed in the synthesis of a number of open-chain and heterocyclic scaffolds, including enantiopure products.

AB - [Structure: see text] Solid-phase synthesis is a rapidly developing area of organic chemistry, of particular importance for medicinal chemistry and chemical biology. Aziridines have previously only rarely been applied in solid-phase synthesis. In the present work, aminolysis of resin-bound, spring-loaded N-nitrobenzenesulfonyl-activated aziridine-2-carboxylic acids has been optimized and employed in the synthesis of a number of open-chain and heterocyclic scaffolds, including enantiopure products.

KW - Amino Alcohols

KW - Aziridines

KW - Carboxylic Acids

KW - Heterocyclic Compounds

KW - Molecular Structure

KW - Stereoisomerism

U2 - 10.1021/ol061304e

DO - 10.1021/ol061304e

M3 - Journal article

C2 - 16836408

SN - 1523-7060

VL - 8

SP - 3371

EP - 3374

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

Aminolysis of resin-bound N-nosylaziridine-2-carboxylic acids

Abstract

Keywords

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