A concise approach to chiral chromenes based on levoglucosenone

Tetrahedron Letters

Volumn 52, Issue 23, 2011, Pages 3026-3028

  Samet, Lexander V ^a   Lutov, Dmitriy N ^a   Firgang, Sergei I ^a   Lyssenko, Konstantine A ^b   Semenov, Victor V ^a  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

2H Chromenes; Beckmann fragmentation; Domino reaction; Levoglucosenone

Indexed keywords

BENZALDEHYDE DERIVATIVE; CHROMENE DERIVATIVE; KETONE DERIVATIVE; LEVOGLUCOSENONE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; BECKMANN REARRANGEMENT; CHIRALITY; MICHAEL ADDITION; STEREOCHEMISTRY; SYNTHESIS;

EID: 79955661308     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.04.004     Document Type: Article

References (38)

1. Ellis, G. P. Chromenes, Chromanones, and Chromones. In The Chemistry of Heterocyclic Compounds; Wiley: New York, 1977; Vol. 31, pp 11-139
2. Hepworth, J. D. Pyrans and Fused Pyrans. Synthesis and Applications. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 3, pp 737-883
3. Fravel, B.W. Pyrans and their Benzo Derivatives: Applications. In Comprehensive Heterocyclic Chemistry III; Katritzky, A. R., Ramsden, C. A., Scriven, E. V. F., Taylor, R. J. K., Eds.; Elsevier: Oxford, Vol. 7, pp 701-726
4. M.C. Brohmer, N. Volz, and S. Bräse Synlett 2009 1383
5. Brimble, M. A.; Gibson, J. S.; Sperry, J. Pyrans and their Benzo Derivatives: Synthesis. In Comprehensive Heterocyclic Chemistry III; Katritzky, A. R., Ramsden, C. A., Scriven, E. V. F., Taylor, R. J. K., Eds.; Elsevier: Oxford, Vol. 7, pp 419-699
6. For a recent mini-review, see: Y.-L. Shi, and M. Shi Org. Biomol. Chem. 2007 1499
7. For some recent examples, see: P.T. Kaye, and X.W. Nocanda J. Chem. Soc., Perkin Trans. 1 2002 1318
8. Y.T. Chen, T.D. Bannister, A. Weiser, E. Griffin, L. Lin, C. Ruiz, M.D. Cameron, S. Schuerer, D. Duckett, T. Schroeter, P. LoGrasso, and Y. Feng Bioorg. Med. Chem. Lett. 18 2008 6406
9. A. Behrenswerth, N. Volz, J. Toräng, S. Hinz, S. Bräse, and C.E. Müller Bioorg. Med. Chem. 17 2009 2842
10. B. Lesch, and S. Bräse Angew. Chem., Int. Ed. 43 2004 115
11. U.K. Ohnemueller, C.F. Nising, M. Nieger, and S. Bräse Eur. J. Org. Chem. 6 2006 1535
12. V.Ya. Sosnovskikh, V.Yu. Korotaev, D.L. Chizhov, I.B. Kutyashev, D.S. Yachevskii, O.N. Kazheva, O.A. Dyachenko, and V.N. Charushin J. Org. Chem. 71 2006 4538
13. J. Xu, C. Yang, M. Wu, and Y. Xie Heterocycles 73 2007 393
14. R. Rios, H. Sunden, I. Ibrahem, and A. Cordova Tetrahedron Lett. 48 2007 2181
15. T. Govender, L. Hojabri, F.M. Moghaddam, and P.I. Arvidsson Tetrahedron: Asymmetry 17 2006 1763
16. H. Li, J. Wang, T. E-Nunu, L. Zu, W. Jiang, S. Wei, and W. Wang Chem. Commun. 2007 507
17. Witczak, Z. J. Ed. Levoglucosenone and Levoglucosans: Chemistry and Applications; ATL Press: Mount Prospect, 1994.
18. Witczak, Z. J.; Tatsuka, K. Eds. Carbohydrate Synthons in Natural Products Chemistry. Synthesis, Functionalization, and Applications. ACS Symposium Series 841; American Chemical Society: Washington, DC, 2003.
19. F. Shafizadeh, D. Ward, and D. Pang Carbohydr. Res. 102 1982 217
20. A.V. Samet, M.E. Niyazymbetov, V.V. Semenov, A.L. Laikhter, and D.H. Evans J. Org. Chem. 61 1996 8786
21. D. Ward, and F. Shafizadeh Carbohydr. Res. 95 1981 155
22. A. Blake, T. Cook, A. Forsyth, R. Gould, and R. Paton Tetrahedron 48 1992 8053
23. For reviews, see Ref. 6 and also: M.S. Miftakhov, F.A. Valeev, and I.N. Gaisina Russ. Chem. Rev. 63 1994 869
24. Witczak, Z. J. New Stereoselective Functionalization of Cellulose-Derived Pyrolysis Derivatives: Levoglucosenone and Its Dimer. In Materials, Chemicals, and Energy from Forest Biomass; ACS Symposium Series 954; American Chemical Society: Washington, DC, 2007; pp 332-349
25. Some recent examples: T. Nishikawa, D. Urabe, and M. Isobe Angew. Chem., Int. Ed. 43 2004 4782
26. L. Awad, R. Demange, Y.-H. Zhu, and P. Vogel Carbohydr. Res. 341 2006 1235
27. A.V. Samet, A.M. Shestopalov, D.N. Lutov, L.A. Rodinovskaya, A.A. Shestopalov, and V.V. Semenov Tetrahedron: Asymmetry 18 2007 1986
28. A.V. Samet, D.N. Lutov, L.D. Konyushkin, Y.A. Strelenko, and V.V. Semenov Tetrahedron: Asymmetry 19 2008 691
29. A.M. Sarotti, R.A. Spanevello, and A.G. Suarez Tetrahedron 65 2009 3502
30. L.F. Tietze Chem. Rev. 96 1996 115
31. Tietze, L. F.; Brasche, G.; Gericke K. M. Domino Reactions in Organic Synthesis, Wiley, 2006.
32. 1,10a = 5.2 Hz for 2′ (cf. Refs. 7b and 8b).
33. 2O (3 ml) and the precipitate filtered and dried.
34. int = 0.0348] were used for further refinement. The absorption correction was performed empirically using APEX2 (Bruker, 2005). Analysis of Fourier density synthesis revealed that the SPh substituent is disordered by two positions with equal occupancies. The refinement converged to wR2 = 0.0531 and GOF = 1.000 for all independent reflections (R1 = 0.0749 was calculated against F for 3104 observed reflections with I >2σ(I)). The refinement of absolute structure led to a Flack parameter (Flack, H.D. Acta Crystallogr., Sect. A 1983, 39, 876-881) equal to 0.00(17). All calculations were performed using SHELXTL PLUS 5.0 (Sheldrick, G.M. Acta Crystallogr., Sect. A 2008, 64, 112-122). CCDC 799240 contains the supplementary crystallographic data for 3b. These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html (or from the CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK; fax: (+44) 1223 336033; or deposit@ccdc.cam.ac.uk.
35. 3 (1 ml) was added dropwise at 0 °C with stirring. The resulting mixture was kept at 0 °C for 40 min and then evaporated to dryness. The residue was chromatographed on silica gel (eluent: hexane/EtOAc, 5:1) to afford nitriles 4a-c.
36. R.E. Gawley Org. React. 35 1988 1
37. Ring opening of 1,3-dioxolan-2-ylium cations is well-documented: C.U. Pittman Jr., S.P. McManus, and J.W. Larsen Chem. Rev. 72 1972 357
38. - evidently attacks the more sterically hindered position of the intermediate cation): Valeev, F. A.; Gorobets, E. V.; Tsypysheva, I. P.; Singizova, G. Sh.; Kalimullina, L. Kh.; Safarov, M. G.; Shitikova, O. V.; Miftakhov, M. S. Chem. Nat. Compd. 2003, 39, 563.