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

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

24 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

Access to Document

10.1021/ol061304e

Cite this

Aminolysis of resin-bound N-nosylaziridine-2-carboxylic acids. / Olsen, Christian A; Christensen, Caspar; Nielsen, Birgitte; Farah, Mohamed M; Mohamed, Farah M; Witt, Matthias; Clausen, Rasmus P ; Kristensen, Jesper L ; Franzyk, Henrik; Jaroszewski, Jerzy W.

In: Organic Letters, Vol. 8, No. 15, 2006, p. 3371-4.

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

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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.",

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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}",

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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

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VL - 8

SP - 3371

EP - 3374

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 15

ER -