An ionic O → α- and β-vinyl carbamoyl translocation of 2-(O-carbamoyl) stilbenes

Organic Letters

Volumn 6, Issue 14, 2004, Pages 2297-2300

  Reed, Mark A ^a   Chang, Michelle T ^a   Snieckus, Victor ^a  

^a QUEEN S UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMOYL PHOSPHATE; STILBENE DERIVATIVE;

ARTICLE; CARBAMOYLATION; CHEMICAL REACTION; CROSS COUPLING REACTION; ELECTRON TRANSPORT; MOLECULAR INTERACTION; REACTION ANALYSIS; SONOGASHIRA REACTION; STEREOCHEMISTRY; SUBSTITUTION REACTION; SUZUKI REACTION;

EID: 3242691776     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049740t     Document Type: Article

References (40)

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14. Stilbene undergoes reductive dilithiation in the presenece of Li metal as discovered by Schlenk in his prognostic contributions to organolithium chemistry: (a) Schlenk, W.; Bergmann, E. Annalen 1928, 483, 106; Houben-Weyl 13/1, 162 ff. Monolithio and 1,1- or 1,2-dilithio stilbene species have been generated mainly by metal-halogen exchange or Li addition to diphenylacetylene: (b) Maercker, A.; Kemmer, M.; Wang, H. C.; Dong, D.-H.; Szwarc, M. Angew Chem., Int. Ed. 1998, 37, 2136-2138. (c) Boche, G. Top. Curr. Chem. 1988, 146, 3-56. Their configurational stability and proton-transfer reactions are highly dependent on solvent and temperature, see: (d) Houben-Weyl, 1952, 13/1, p 133 and 1989E, 19d, pp 176, 483, 498. (e) Maercker, A. In Sapse, A. M., Schleyer, P. von R. Lithium Chemistry. A Theoretical and Experimental Overview, Wiley: New York, 1995; p 477.
15. Stilbene undergoes reductive dilithiation in the presenece of Li metal as discovered by Schlenk in his prognostic contributions to organolithium chemistry: (a) Schlenk, W.; Bergmann, E. Annalen 1928, 483, 106; Houben-Weyl 13/1, 162 ff. Monolithio and 1,1- or 1,2-dilithio stilbene species have been generated mainly by metal-halogen exchange or Li addition to diphenylacetylene: (b) Maercker, A.; Kemmer, M.; Wang, H. C.; Dong, D.-H.; Szwarc, M. Angew Chem., Int. Ed. 1998, 37, 2136-2138. (c) Boche, G. Top. Curr. Chem. 1988, 146, 3-56. Their configurational stability and proton-transfer reactions are highly dependent on solvent and temperature, see: (d) Houben-Weyl, 1952, 13/1, p 133 and 1989E, 19d, pp 176, 483, 498. (e) Maercker, A. In Sapse, A. M., Schleyer, P. von R. Lithium Chemistry. A Theoretical and Experimental Overview, Wiley: New York, 1995; p 477.
16. Stilbene undergoes reductive dilithiation in the presenece of Li metal as discovered by Schlenk in his prognostic contributions to organolithium chemistry: (a) Schlenk, W.; Bergmann, E. Annalen 1928, 483, 106; Houben-Weyl 13/1, 162 ff. Monolithio and 1,1- or 1,2-dilithio stilbene species have been generated mainly by metal-halogen exchange or Li addition to diphenylacetylene: (b) Maercker, A.; Kemmer, M.; Wang, H. C.; Dong, D.-H.; Szwarc, M. Angew Chem., Int. Ed. 1998, 37, 2136-2138. (c) Boche, G. Top. Curr. Chem. 1988, 146, 3-56. Their configurational stability and proton-transfer reactions are highly dependent on solvent and temperature, see: (d) Houben-Weyl, 1952, 13/1, p 133 and 1989E, 19d, pp 176, 483, 498. (e) Maercker, A. In Sapse, A. M., Schleyer, P. von R. Lithium Chemistry. A Theoretical and Experimental Overview, Wiley: New York, 1995; p 477.
17. Stilbene undergoes reductive dilithiation in the presenece of Li metal as discovered by Schlenk in his prognostic contributions to organolithium chemistry: (a) Schlenk, W.; Bergmann, E. Annalen 1928, 483, 106; Houben-Weyl 13/1, 162 ff. Monolithio and 1,1- or 1,2-dilithio stilbene species have been generated mainly by metal-halogen exchange or Li addition to diphenylacetylene: (b) Maercker, A.; Kemmer, M.; Wang, H. C.; Dong, D.-H.; Szwarc, M. Angew Chem., Int. Ed. 1998, 37, 2136-2138. (c) Boche, G. Top. Curr. Chem. 1988, 146, 3-56. Their configurational stability and proton-transfer reactions are highly dependent on solvent and temperature, see: (d) Houben-Weyl, 1952, 13/1, p 133 and 1989E, 19d, pp 176, 483, 498. (e) Maercker, A. In Sapse, A. M., Schleyer, P. von R. Lithium Chemistry. A Theoretical and Experimental Overview, Wiley: New York, 1995; p 477.
18. Stilbene undergoes reductive dilithiation in the presenece of Li metal as discovered by Schlenk in his prognostic contributions to organolithium chemistry: (a) Schlenk, W.; Bergmann, E. Annalen 1928, 483, 106; Houben-Weyl 13/1, 162 ff. Monolithio and 1,1- or 1,2-dilithio stilbene species have been generated mainly by metal-halogen exchange or Li addition to diphenylacetylene: (b) Maercker, A.; Kemmer, M.; Wang, H. C.; Dong, D.-H.; Szwarc, M. Angew Chem., Int. Ed. 1998, 37, 2136-2138. (c) Boche, G. Top. Curr. Chem. 1988, 146, 3-56. Their configurational stability and proton-transfer reactions are highly dependent on solvent and temperature, see: (d) Houben-Weyl, 1952, 13/1, p 133 and 1989E, 19d, pp 176, 483, 498. (e) Maercker, A. In Sapse, A. M., Schleyer, P. von R. Lithium Chemistry. A Theoretical and Experimental Overview, Wiley: New York, 1995; p 477.
19. Stilbene undergoes reductive dilithiation in the presenece of Li metal as discovered by Schlenk in his prognostic contributions to organolithium chemistry: (a) Schlenk, W.; Bergmann, E. Annalen 1928, 483, 106; Houben-Weyl 13/1, 162 ff. Monolithio and 1,1- or 1,2-dilithio stilbene species have been generated mainly by metal-halogen exchange or Li addition to diphenylacetylene: (b) Maercker, A.; Kemmer, M.; Wang, H. C.; Dong, D.-H.; Szwarc, M. Angew Chem., Int. Ed. 1998, 37, 2136-2138. (c) Boche, G. Top. Curr. Chem. 1988, 146, 3-56. Their configurational stability and proton-transfer reactions are highly dependent on solvent and temperature, see: (d) Houben-Weyl, 1952, 13/1, p 133 and 1989E, 19d, pp 176, 483, 498. (e) Maercker, A. In Sapse, A. M., Schleyer, P. von R. Lithium Chemistry. A Theoretical and Experimental Overview, Wiley: New York, 1995; p 477.
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22. 2/DMF.
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24. For purification purposes, the intermediate boronic acid was first converted into its crystalline diethanolamine adduct, which was subjected to treatment with pinacol in 50% citric acid/hexane mixture to give analytically pure 13.
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27. CCDC 235465 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via the Internet at www.ccdc.cam.ac.uk/data_request/cif,byemailingdata_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK, fax: +44 1223 336033.
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33. Prepared by the method in: Shen, W. Synlett 2000, 737-739.
34. Stereoselective trans coupling of 1,2-dibromostilbenes is precedented; see ref 20 and: Gaukroger, K.; Hadfield, J. A.; Hepworth, L. A.; Lawrence, N. J.; McGown, A. T. J. Org. Chem. 2001, 66, 8135-8138.
35. 27d: Yoneda, E.; Sugioka, T.; Hirao, K.; Zhang, S.-W.; Takahashi, S. J. Chem. Soc., Perkin Trans. 1 1998, 3, 477-483. 27b: see ref 3d. 27f: see Supporting Information.
36. Michael addition of LDA followed by carbamoyl transfer and LDA elimination, envisaged only for the α-vinyl rearrangement result; a type of an intramolecular Baylis-Hillman reaction (ref 19) is an alternate, less likely, explanation.
37. a = 37.2, see: Fraser, R. R.; Bresse, M.; Mansour, T. S. J. Am. Chem. Soc. 1983, 105, 7790-7791.
38. Stereoselective construction of stilbene is of interest in context of natural product, bioactive molecule, and material science substance synthesis; see inter alia: Rathore, R.; Deselinicu, M. I.; Burns, C. L. J. Am. Chem. Soc. 2002, 124, 14832-14833. Jeffery, T.; Ferber, B. Teterahedron Lett. 2003, 44, 193-197. Kabalka, G. W.; Wu, Z.; Ju, Y. Tetrahedron Lett. 2001, 42, 4759-4760.
39. Stereoselective construction of stilbene is of interest in context of natural product, bioactive molecule, and material science substance synthesis; see inter alia: Rathore, R.; Deselinicu, M. I.; Burns, C. L. J. Am. Chem. Soc. 2002, 124, 14832-14833. Jeffery, T.; Ferber, B. Teterahedron Lett. 2003, 44, 193-197. Kabalka, G. W.; Wu, Z.; Ju, Y. Tetrahedron Lett. 2001, 42, 4759-4760.
40. Stereoselective construction of stilbene is of interest in context of natural product, bioactive molecule, and material science substance synthesis; see inter alia: Rathore, R.; Deselinicu, M. I.; Burns, C. L. J. Am. Chem. Soc. 2002, 124, 14832-14833. Jeffery, T.; Ferber, B. Teterahedron Lett. 2003, 44, 193-197. Kabalka, G. W.; Wu, Z.; Ju, Y. Tetrahedron Lett. 2001, 42, 4759-4760.