Bicatalytic multistep reactions en route to the one-pot total synthesis of complex molecules: easy access to chromene and 1,2-dihydroquinoline derivatives from simple substrates

Article English OPEN
Giorgi, Pascal D. ; Miedziak, Peter John ; Edwards, Jennifer Kelly ; Hutchings, Graham John ; Antoniotti, Sylvain (2017)

By combining nanocatalysis and base-catalysis, a novel one-pot multistep process was found for the synthesis of substituted heterocycles of biological relevance from simple substrates. It is based on an initial Au/O2 oxidation of allylic alcohols followed by a base-catalysed tandem hetero-Michael/aldolisation/crotonisation with ortho-hydroxy or ortho-amino benzaldehydes. The flexibility of the reaction even allowed the benzaldehyde partner to be prepared in situ in an example of one-pot/5-steps process.
  • References (41)
    41 references, page 1 of 5

    [1] a) P. Anastas, J. Warner, Green chemistry: theory and practice, Oxford University Press, Oxford, 1998, 135. b) M. Poliakoff, P. Anastas, Nature 2001, 413, 257. c) R. A. Sheldon, Chem. Commun. 2008, 3352-3365. d) B. M. Trost, Science 1991, 254, 1471-1477.

    [2] T. L. Lohr, T. J. Marks, Nat. Chem. 2015, 7, 477-482.

    [3] a) X. Li, L. Yang, C. Peng, X. Xie, H.-J. Leng, B. Wang, Z.-W. Tang, G. He, L. Ouyang, W. Huang, B. Han, Chem. Commun. 2013, 49, 8692-8694. b) R. C. Wende, P. R. Schreiner, Green Chem. 2012, 14, 1821-1849.

    [4] a) Y. Jeong, Y. Moon, S. Hong, Org. Lett. 2015, asap. b) L. Li, X.-H. Xia, Y. Wang, P. P. Bora, Q. Kang, Adv. Synth. Catal. 2015, 357, 2089-2097. c) Y. Oonishi, A. Gomez-Suarez, A. R. Martin, Y. Makida, A. M. Z. Slawin, S. P. Nolan, Chem. - Eur. J. 2014, 20, 13507-13510.

    [5] C. A. Denard, M. J. Bartlett, Y. Wang, L. Lu, J. F. Hartwig, H. Zhao, ACS Catalysis 2015, 5, 3817-3822.

    [6] B. Simmons, A. M. Walji, D. W. C. MacMillan, Angew. Chem. 2009, 121, 4413-4417; Angew. Chem. Int. Ed. 2009, 48, 4349-4353.

    [7] a) G. He, F. Wu, W. Huang, R. Zhou, L. Ouyang, B. Han, Adv. Synth. Catal. 2014, 356, 2311-2319. b) C. B. Jacobsen, L. Albrecht, J. Udmark, K. A. Joergensen, Org. Lett. 2012, 14, 5526-5529. c) Y. Liu, M. Nappi, E. C. Escudero-Adan, P. Melchiorre, Org. Lett. 2012, 14, 1310-1313.

    [8] D. Hager, D. W. C. MacMillan, J. Am. Chem. Soc. 2014, 136, 16986-16989.

    [9] a) A. Noble, S. J. McCarver, D. W. C. MacMillan, J. Am. Chem. Soc. 2015, 137, 624-627. b) C. Vila, ChemCatChem 2015, 7, 1790-1793. c) L. Chu, J. M. Lipshultz, D. W. C. MacMillan, Angew. Chem. 2015, 127, 8040-8044; Angew. Chem. Int. Ed. 2015, 54, 7929-7933.

    [10] K. Akagawa, S. Takigawa, E. Mano, K. Kudo, Tetrahedron Lett. 2011, 52, 770-773.

  • Metrics
    0
    views in OpenAIRE
    0
    views in local repository
    29
    downloads in local repository

    The information is available from the following content providers:

    From Number Of Views Number Of Downloads
    Online Research @ Cardiff - IRUS-UK 0 29
Share - Bookmark