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

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

Lee Bollans,^a John Bacsa,^a Jonathan A. Iggo,^a Gareth A. Morris^b and Andrew V. Stachulski*^a

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* Corresponding authors

^a Robert Robinson Laboratories, Department of Chemistry, University of Liverpool, Liverpool, UK
E-mail: stachuls@liv.ac.uk
Fax: 44 (0) 151 794 3588
Tel: 44 (0) 151 794 3542

^b School of Chemistry, University of Manchester, Oxford Rd., Manchester, UK

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.

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Article information

DOI: https://doi.org/10.1039/B912963D
Article type: Paper
Submitted: 01 Jul 2009
Accepted: 30 Jul 2009
First published: 02 Sep 2009

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Org. Biomol. Chem., 2009,7, 4531-4538

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

L. Bollans, J. Bacsa, J. A. Iggo, G. A. Morris and A. V. Stachulski, Org. Biomol. Chem., 2009, 7, 4531 DOI: 10.1039/B912963D

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Organic & Biomolecular Chemistry