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Wang R, Bojase G, Willis AC, et al. Nitroso-dienophile additions to dendralenes: a short synthesis of branched aminosugars. Org Lett. 2012;14(22):5652-5doi: 10.1021/ol302619r.
Wang, R., Bojase, G., Willis, A. C., Paddon-Row, M. N., & Sherburn, M. S. (2012). Nitroso-dienophile additions to dendralenes: a short synthesis of branched aminosugars. Organic letters, 14(22), 5652-5. https://doi.org/10.1021/ol302619r
Wang, Ruomeng, et al. "Nitroso-dienophile additions to dendralenes: a short synthesis of branched aminosugars." Organic letters vol. 14,22 (2012): 5652-5. doi: https://doi.org/10.1021/ol302619r
Wang R, Bojase G, Willis AC, Paddon-Row MN, Sherburn MS. Nitroso-dienophile additions to dendralenes: a short synthesis of branched aminosugars. Org Lett. 2012 Nov 16;14(22):5652-5. doi: 10.1021/ol302619r. Epub 2012 Oct 30. PMID: 23106239.
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Org Lett. 2012 Nov 16;14(22):5652-5. doi: 10.1021/ol302619r. Epub 2012 Oct 30.

Nitroso-dienophile additions to dendralenes: a short synthesis of branched aminosugars.

Organic letters

Ruomeng Wang, Gomotsang Bojase, Anthony C Willis, Michael N Paddon-Row, Michael S Sherburn

Affiliations

  1. Australian Research Council Centre of Excellence for Free Radical Chemistry and Biotechnology, Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia.

PMID: 23106239 DOI: 10.1021/ol302619r

Abstract

The first heteroatom-based dienophile cycloadditions to cross-conjugated alkenes ([n]dendralenes) are reported. Nitroso-dienophiles undergo smooth single and double Diels-Alder additions to the parent dendralenes with orientational regio- and stereoselectivity and, notably, with reactivity that depends upon the parity of the [n]dendralene. The first crystal structure of a cross-conjugated hexaene is reported. Vasella's nitroso-sugar reagent gives a highly enantiomerically enriched double cycloadduct with [3]dendralene. This bicyclic oxazine is successively dihydroxylated and then ring-opened to form a branched chain diamino tetrol.

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