The acyl nitroso Diels-Alder (ANDA) reaction of sorbate derivatives: An X-ray and 15N NMR study with an application to amino-acid synthesis

Lee Bollans; John Bacsa; Jonathan A. Iggo; Gareth A. Morris; Andrew V. Stachulski

doi:10.1039/b912963d

The acyl nitroso Diels-Alder (ANDA) reaction of sorbate derivatives: An X-ray and 15N NMR study with an application to amino-acid synthesis

Lee Bollans, John Bacsa, Jonathan A. Iggo, Gareth A. Morris, Andrew V. Stachulski

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

Abstract

We present a study of the acyl nitroso Diels-Alder (ANDA) reaction of sorbate esters and sorbic alcohol derivatives, using alkoxycarbonyl nitroso dienophiles. An optimisation of the reaction conditions for ethyl sorbate is first presented, and the product is used in an efficient synthesis of 5-methylornithine. Structure-reactivity trends in sorbic alcohol (E,E-2,4-hexadien-1-ol) and its acylated analogues are then discussed. We present single-crystal X-ray structural proof for key adducts in both series and present in detail a novel HMBC/HSQC (1H-15N) criterion for ready distinction of regioisomers arising from such ANDA reactions. © 2009 The Royal Society of Chemistry.

Original language	English
Pages (from-to)	4531-4538
Number of pages	7
Journal	Organic and Biomolecular Chemistry
Volume	7
Issue number	21
DOIs	https://doi.org/10.1039/b912963d
Publication status	Published - 2009

Keywords

c-nitrosocarbonyl compounds
cycloaddition
dienophiles
inhibitors
lactams
dienes

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10.1039/b912963d

CCDC 725211: Experimental Crystal Structure Determination
Bollans, L. (Contributor), Bacsa, J. (Contributor), Iggo, J. A. (Contributor), Morris, G. (Contributor) & Stachulski, A. V. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2010
DOI: 10.5517/ccsbmxm, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccsbmxm&sid=DataCite
Dataset
CCDC 738892: Experimental Crystal Structure Determination
Bollans, L. (Contributor), Bacsa, J. (Contributor), Iggo, J. A. (Contributor), Morris, G. (Contributor) & Stachulski, A. V. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2010
DOI: 10.5517/ccssw7n, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccssw7n&sid=DataCite
Dataset

Cite this

@article{84742d85d60e40849259738cf5df4876,

title = "The acyl nitroso Diels-Alder (ANDA) reaction of sorbate derivatives: An X-ray and 15N NMR study with an application to amino-acid synthesis",

abstract = "We present a study of the acyl nitroso Diels-Alder (ANDA) reaction of sorbate esters and sorbic alcohol derivatives, using alkoxycarbonyl nitroso dienophiles. An optimisation of the reaction conditions for ethyl sorbate is first presented, and the product is used in an efficient synthesis of 5-methylornithine. Structure-reactivity trends in sorbic alcohol (E,E-2,4-hexadien-1-ol) and its acylated analogues are then discussed. We present single-crystal X-ray structural proof for key adducts in both series and present in detail a novel HMBC/HSQC (1H-15N) criterion for ready distinction of regioisomers arising from such ANDA reactions. {\textcopyright} 2009 The Royal Society of Chemistry.",

keywords = "c-nitrosocarbonyl compounds, cycloaddition, dienophiles, inhibitors, lactams, dienes",

author = "Lee Bollans and John Bacsa and Iggo, {Jonathan A.} and Morris, {Gareth A.} and Stachulski, {Andrew V.}",

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T1 - The acyl nitroso Diels-Alder (ANDA) reaction of sorbate derivatives: An X-ray and 15N NMR study with an application to amino-acid synthesis

AU - Bollans, Lee

AU - Bacsa, John

AU - Iggo, Jonathan A.

AU - Morris, Gareth A.

AU - Stachulski, Andrew V.

N1 - 506SH Times Cited:0 Cited References Count:32

PY - 2009

Y1 - 2009

N2 - We present a study of the acyl nitroso Diels-Alder (ANDA) reaction of sorbate esters and sorbic alcohol derivatives, using alkoxycarbonyl nitroso dienophiles. An optimisation of the reaction conditions for ethyl sorbate is first presented, and the product is used in an efficient synthesis of 5-methylornithine. Structure-reactivity trends in sorbic alcohol (E,E-2,4-hexadien-1-ol) and its acylated analogues are then discussed. We present single-crystal X-ray structural proof for key adducts in both series and present in detail a novel HMBC/HSQC (1H-15N) criterion for ready distinction of regioisomers arising from such ANDA reactions. © 2009 The Royal Society of Chemistry.

AB - We present a study of the acyl nitroso Diels-Alder (ANDA) reaction of sorbate esters and sorbic alcohol derivatives, using alkoxycarbonyl nitroso dienophiles. An optimisation of the reaction conditions for ethyl sorbate is first presented, and the product is used in an efficient synthesis of 5-methylornithine. Structure-reactivity trends in sorbic alcohol (E,E-2,4-hexadien-1-ol) and its acylated analogues are then discussed. We present single-crystal X-ray structural proof for key adducts in both series and present in detail a novel HMBC/HSQC (1H-15N) criterion for ready distinction of regioisomers arising from such ANDA reactions. © 2009 The Royal Society of Chemistry.

KW - c-nitrosocarbonyl compounds

KW - cycloaddition

KW - dienophiles

KW - inhibitors

KW - lactams

KW - dienes

U2 - 10.1039/b912963d

DO - 10.1039/b912963d

M3 - Article

SN - 1477-0520

VL - 7

SP - 4531

EP - 4538

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 21

ER -

The acyl nitroso Diels-Alder (ANDA) reaction of sorbate derivatives: An X-ray and 15N NMR study with an application to amino-acid synthesis

Abstract

Keywords

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Datasets

CCDC 725211: Experimental Crystal Structure Determination

CCDC 738892: Experimental Crystal Structure Determination

Cite this