Catalytic asymmetric synthesis of chromenes and tetrahydroquinolines via sequential allylic alkylation and intramolecular Heck coupling

Chemical Communications

Volumn 48, Issue 31, 2012, Pages 3712-3714

  Hornillos, Valentín ^a   Van Zijl, Anthoni W ^a   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; CHROMENE DERIVATIVE; COPPER; EXOCYCLIC DOUBLE BOND; QUINOLINE DERIVATIVE;

ALKYLATION; ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CHIRALITY; ENANTIOSELECTIVITY; GRIGNARD REACTION; HECK REACTION; HYDROBORATION; HYDROGENATION; SUBSTITUTION REACTION;

EID: 84860183729     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c2cc30395g     Document Type: Article

References (25)

1. G. P. Ellis and I. M. Lockhart, The Chemistry of Heterocyclic Compounds. Vol. 31: Chromenes, Chromanones, and Chromones, ed. G. P. Ellis, Wiley-VCH, 2007, pp. 1–1196
2. J. D. Hepworth, C. D. Gabbutt and B. M. Heron, in Comprehensive Heterocyclic Chemistry II: Pyrans and Their Benzo Derivatives: Synthesis, ed. A. R. Katritzky, C. W. Rees and E. F. V. Scriven, Pergamon Press, Oxford, 1996, vol. 5, pp. 351–468
3. H. C. Shen, Tetrahedron, 2009, 65, 3931-3952
4. M. G. Núñez, P. García, R. F. Moro, D. Díez, Tetrahedron, 2010, 66, 2089-2109
5. V. Sridharan, P. A. Suryavanshi, J. C. Menendez, Chem. Rev., 2011, 111, 7157
6. Z.-X. Jia, Y.-C. Luo, P.-F. Xu, Org. Lett., 2011, 13, 832-835
7. P. M. Dewick, Medicinal Natural Products—A Biosynthetic Approach, Wiley, Chichester, 2nd edn, 2001
8. G. Satyanarayana, D. Pflästerer, G. Helmchen, Eur. J. Org. Chem., 2011, 6877-6886
9. F. López, A. W. van Zijl, A. J. Minnaard, B. L. Feringa, Chem. Commun., 2006, 409
10. K. Geurts, S. P. Fletcher, B. L. Feringa, J. Am. Chem. Soc., 2006, 128, 15572
11. S. Harutyunyan, T. den Hartog, K. Geurts, A. J. Minnaard, B. L. Feringa, Chem. Rev., 2008, 108, 2824
12. A. Alexakis, J. E. Bäckvall, N. Krause, O. Pàmies, M. Diéguez, Chem. Rev., 2008, 108, 2796
13. A. W. van Zijl, F. López, A. J. Minnaard, B. L. Feringa, J. Org.Chem., 2007, 72, 2558
14. T. den Hartog, B. Maciá, A. J. Minnaard, B. L. Feringa, Adv. Synth. Catal., 2010, 352, 999
15. F. Giacomina, D. Riat, A. Alexakis, Org. Lett., 2010, 12, 1156
16. J. F. Teichert, S. Zhang, A. W. van Zijl, J. W. Slaa, A. J. Minnaard, B. L. Feringa, Org. Lett., 2010, 12, 4658
17. B. Mao, K. Geurts, M. Fañanas-Mastral, A. W. van Zijl, S. P. Fletcher, A. J. Minnaard, B. L. Feringa, Org. Lett., 2011, 13, 948
18. R. Imbos, A. J. Minnaard, B. L. Feringa, J. Am. Chem. Soc., 2002, 124, 184
19. A. B. Dounay, L. E. Overman, Chem. Rev., 2003, 103, 2945
20. I. P. Beletskaya, A. V. Cheprakov, Chem. Rev., 2000, 100, 3009
21. V. Calò, A. Nacci, A. Monopoli, P. Cotugno, Angew. Chem., Int. Ed., 2009, 48, 6101
22. R. H. Grubbs, Angew. Chem., Int. Ed., 2006, 45, 3760
23. L. Minuti, E. Ballerini, J. Org. Chem., 2011, 76, 5392
24. A. Kreier, R. Fröhlich, E. Wegelius, D. Hoppe, Synthesis, 2000, 1391
25. T. Miura, M. Yamauchi, A. Kosaka, M. Murakami, Angew. Chem., Int. Ed., 2010, 49, 4955