Efficient rhodium-catalyzed conjugate addition of arylboronic acids to unsaturated furano esters for the highly stereoselective synthesis of four natural trisubstituted furanolignans

European Journal of Organic Chemistry

Volumn , Issue 25, 2009, Pages 4225-4229

  Mondière, Aurélie ^a   Pousse, Guillaume ^a   Bouyssi, Didier ^a   Balme, Geneviève ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

Boronic acids; Conjugate addition; Lignans; Microwave chemistry; Rhodium

Indexed keywords

EID: 68949132545     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900643     Document Type: Article

References (41)

1. a) W. D. MacRae, G. H. N. Towers, Phytochemistry 1984, 23, 1207-1220;
2. b) D. A. Whiting, Nat. Prod. Rep. 1985, 2, 191-211;
3. D. A. Whiting, Nat. Prod. Rep. 1990, 7, 349-364;
4. c) R. S. Ward, Nat. Prod. Rep. 1995, 12, 183-205.
5. D. C. Ayres, J. D. Loike, in Lignans: Chemical, Biological and Clinical Properties, Cambridge University Press, Cambridge, 1990;
6. O. R. Gottlieb, in New Natural Products and Plant Drugs with Pharmacological, Biological or Therapeutical Activity, Springer, Berlin, 1987, pp. 227-248;
7. R. S. Ward, Nat. Prod. Rep. 1999, 16, 75-96.
8. D. R. Stevens, D. A. Whiting, J. Chem. Soc. Perkin Trans. 1 1992, 633-637;
9. S. Yamauchi, T. Tanaka, Y. Kinoshita, J. Chem. Soc. Perkin Trans. 1 2001, 2158-2160;
10. B. Banerjee, S. C. Roy, S. Garçon, S. Vassiliou, M. Cavicchioli, B. Hartmann, N. Monteiro, G. Balme, J. Org. Chem. 2001, 66, 4069-4073.
11. L. Ferrié, D. Bouyssi, G. Balme, Org. Lett. 2005, 7, 3143-3146.
12. P. Perlmutter, in Conjugate Addition Reactions in Organic Synthesis, Pergamon Press, Oxford, 1992;
13. A. Alexakis, in Transition Metals for Organic Synthesis, vol. 1 (Eds: M. Beller, C. Bolm), Wiley-WCH, Weinheim, 1998, chapter 3.8.
14. J. M. Mellor, G. Reid, A. H. El-Sagheer, E.-S. H. El-Tamany, Tetrahedron 2000, 56, 10039-10055.
15. a) First report: M. Sakai, H. Hayashi, N. Miyaura, Organometallics 1997, 16, 4229-4231;
16. For recent reviews, see: b) T. Hayashi, Synlett 2001, 879-887;
17. c) K. Fagnou, M. Lautens, Chem. Rev. 2003, 103, 169-196;
18. d) T. Hayashi, K. Yamasaki, Chem. Rev. 2003, 103, 2829-2844;
19. e) T. Hayashi, Pure Appl. Chem. 2004, 76, 465-475;
20. K. Yoshida, T. Hayashi in Boronic Acids (Ed.: D. G. Hall), Wiley-VCH, Weinheim, 2005, pp. 171-201;
21. K. Yoshida, T. Hayashi in Modern Rhodium-Catalyzed Organic Reactions (Ed.: P. A. Evans), Wiley-VCH, Weinheim, 2005, pp. 55-78;
22. N. Miyaura, Bull. Chem. Soc. Jpn. 2008, 81, 1535-1553.
23. A low yield is generally observed for the Rh-catalyzed addition of organoboronic acids to trisubstituted esters due to their steric hindrance, see: S. Sakuma, M. Sakai, R. Itooka, N. Miyaura, J. Org. Chem. 2000, 65, 5951-5955.
24. Unsaturated furano ester 6 has been readily prepared from commercially available 2,3-dihydrofuran according to slightly modified literature procedures, see: B. M. Trost, J. M. Balkovec, M. K.-T. Mao, J. Am. Chem. Soc. 1986, 108, 4974-4983.
25. R. Itooka, Y. Iguchi, N. Miyaura, J. Org. Chem. 2003, 68, 6000-6004.
26. 1HNMR spectra of the respective methoxy proton signals, which appeared upfield in the trans isomer in comparison with the corresponding signals in the cis isomer due to the anisotropic effect of the adjacent aryl group. Stereochemical assignments of the two diastereomers may also be deduced by comparison of NMR signals of related substrates, see: D. J. Aldous, A. S. Batsanov, D. S. Yufit, A. J. Dalençon, W. M. Dutton, P. G. Steel, Org. Biomol. Chem. 2006, 4, 2912-2927.
27. CCDC-731725, contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
28. a) P. S. Iyer, M. O'Malley, M. C. Lucas, Tetrahedron Lett. 2007, 48, 4413-4418; for some recent reviews and books on microwave-assisted syntheses, see:
29. b) P. Lidström, J. Tierney, B. Wathey, J. Westman, Tetrahedron 2001, 57, 9225-9283;
30. c) Microwaves in Organic Synthesis (Ed.: A. Loupy), Wiley-VCH, Weinheim, 2002;
31. d) Microwave Assisted Organic Synthesis (Eds.: J. P. Tierney, P. Lidström), Blackwell, Oxford, UK, 2005.
32. a) R. A. Batey, A. N. Thadani, D. V. Smil, Org. Lett. 1999, 1, 1683-1686;
33. for reviews on organotrifluoroborate salts, see: b) G. A. Molander, R. Figueroa, Aldrichim. Acta 2005, 38, 49-56;
34. c) S. Darses, J.-P. Genêt, Eur. J. Org. Chem. 2003, 4313-4327.
35. a) A. P. Krapcho, A. J. Lovely, Tetrahedron Lett. 1973, 14, 957-960;
36. b) A. P. Krapcho, Synthesis 1982, 805-822;
37. A. P. Krapcho, Synthesis 1982, 893-914.
38. Y. M. Kim, T. W. Kwon, S. K. Chung, M. B. Smith, Synth. Commun. 1999, 29, 343-350.
39. Selective formation of 4a is assumed to result from protonation of the intermediate enolate by TFA followed by elimination of methanol in acidic medium.
40. The use of additional quantities of rhodium catalyst, longer reaction times or higher temperatures did not increase the isolated yields of 10a
41. a) S. M. Miles, S. P. Marsden, R. J. Leatherbarrow, W. J. Coates, J. Org. Chem. 2004, 69, 6874-6882.