Synthesis of cis-vinyltrimethylstannanes and cis-vinylpinacolboronates in a two-step highly regio and stereoselective process

Tetrahedron

Volumn 65, Issue 39, 2009, Pages 8297-8305

  Mirzayans, Paul Malek ^a   Pouwer, Rebecca H ^a   Williams, Craig M ^a   Bernhardt, Paul V ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; LITHIUM; TELLURIUM; TIN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS;

EID: 69049119157     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.06.092     Document Type: Article

References (63)

1. See:. Yu T.-Q., Fu Y., Liu L., and Guo Q.X. J. Org. Chem. 71 (2006) 6157 and references therein
2. Brandänge S., and Leijonmarck H. Chem. Commun. (2004) 292 and references therein
3. Pouwer R.H., Schill H., Williams C.M., and Bernhardt P.V. Eur. J. Org. Chem. (2007) 4699
4. Stille J.K. Angew. Chem., Int. Ed. Engl. 25 (1986) 508
5. Miyaura N., and Suzuki A. Chem. Rev. 95 (1995) 2457
6. For a good comparative demonstration of both protocols, see. López S., Montenegro J., and Saá C. J. Org. Chem. 72 (2007) 9572 and references therein
7. Smith N.D., Mancuso J., and Lautens M. Chem. Rev. 100 (2000) 3257
8. Gevorgyan V., Liu J.X., and Yamamoto Y. Chem. Commun. 1 (1998) 37
9. Asao N., Liu J.X., Sudoh T., and Yamamoto Y. J. Org. Chem. 61 (1996) 4568
10. Rim C., and Son D.Y. Org. Lett. 5 (2003) 3443
11. Kikukawa K., Umekawa H., Wada F., and Matsuda T. Chem. Lett. (1988) 881
12. Bickley J.F., Roberts S.M., Santoro M.G., and Snape T.J. Tetrahedron 60 (2004) 2569
13. Bialy L., and Waldmann H. Chem.-Eur. J. 10 (2004) 2759
14. Lipshutz B., Keil R., and Barton J. Tetrahedron Lett. 33 (1992) 5861
15. Cochran J.C., Philips H.K., Tom S., Hurd A.R., and Bronk B.S. Organometallics 13 (1994) 947
16. Thiele C.M., and Mitchell T.N. Eur. J. Org. Chem. (2004) 337
17. Miura K., Wang D., Matsumoto Y., and Hosomi A. Org. Lett. 7 (2005) 503
18. Srebnik M., Bhat N.G., and Brown H.C. Tetrahedron Lett. 29 (1988) 2635
19. Soderquist J.A., Rane A.M., Matos K., and Ramos J. Tetrahedron Lett. 36 (1995) 6847
20. Molander G.A., and Ellis N.M. J. Org. Chem. 73 (2008) 6841
21. Deloux L., and Srebnik M. J. Org. Chem. 59 (1994) 6871
22. Pereira S., and Srebnik M. Organometallics 14 (1995) 3127
23. Deloux L., Skrzypczak-Jankun E., Cheesman B.V., and Srebnik M. J. Am. Chem. Soc. 116 (1994) 10302
24. Deloux L., Srebnik M., and Sabat M. J. Org. Chem. 60 (1995) 3276
25. Tucker C.E., Davidson J., and Knochel P. J. Org. Chem. 57 (1992) 3482
26. Ohmura T., Yamamoto Y., and Miyaura N. J. Am. Chem. Soc. 122 (2000) 4990
27. Hoshi M., Shirakawa K., and Okimoto M. Tetrahedron Lett. 48 (2007) 8475
28. Khramov D.M., Rosen E.L., Er J.A.V., Vu P.D., Lynch V.M., and Bielawski C.W. Tetrahedron 64 (2008) 6853
29. Campbell Jr. J.B., and Molander G.A. J. Organomet. Chem. 156 (1978) 71
30. Negishi E.-i., Williams R.M., Lew G., and Yoshida T. J. Organomet. Chem. 92 (1975) C4
31. Matteson D.S., and Majumdar D. Organometallics 2 (1983) 230
32. Kabalka G.W., Akula M.R., and Zhang J. Nucl. Med. Biol. 30 (2003) 369
33. Lee T., Baik C., Jung I., Song K.H., Kim S., Kim D., Kang S.O., and Ko J. Organometallics 23 (2004) 4569
34. Barross S.M., Dabdoub M.J., Dabdoub V.M.B., and Comasseto J.V. Organometallics 8 (1989) 1661
35. Huang X., Liang C., Qing X., and He Q. J. Org. Chem. 66 (2001) 74 and references therein
36. Zeni G., Lüdtke D.S., Panatieri R.B., and Braga A.L. Chem. Rev. 106 (2006) 1032
37. Petragnani, N.; Stefani, H. A. Tellurium in Organic Chemistry, Second, Updated and Enlarged Edition; ACADEMIC PRESS: Amsterdam, Netherlands, 2007.
38. A preliminary communication describing the synthesis of cis-vinyltrimethylstannes has been reported, see. Mirzayans P.M., Pouwer R.H., and Williams C.M. Org. Lett. 10 (2008) 3861
39. Stefani H.A., Costa I.M., and Zeni G. Tetrahedron Lett. 40 (1999) 9215
40. Vieira M.L., Zinn F.K., and Comasseto J.V. J. Braz. Chem. Soc. 12 (2001) 586
41. Huang X., and Liang C.-G. Synth. Commun. 30 (2000) 1903 and references therein. When employing these methods one should also consider Refs. 14, 9 and 15
42. Lenardão E.J., Mendes S.R., Ferreira P.C., Perin G., Silveira C.C., and Jacob R.G. Tetrahedron Lett. 47 (2006) 7439
43. Balfe M.P., Chaplin C.A., and Phillips H. J. Chem. Soc., Chem. Commun. (1938) 341
44. Brown H.C., and Cole T.E. Organometallics 2 (1983) 1316
45. Stefani H.A., Guadagnin R.C., Keppler A.F., Botteselle G.V., Comasseto J.V., and Suganuma C.A. Beilstein J. Org. Chem. 4 (2008) No. 9
46. Stefani H.A., Cella R., Dörr F.A., Pereira C.M.P., Zeni G., and Gomes Jr. M. Tetrahedron Lett. 46 (2005) 563
47. Cella R., Orfão A.T.G., and Stefani H.A. Tetrahedron Lett. 47 (2006) 5075
48. Cella R., and Stefani H.A. Tetrahedron 62 (2006) 5656
49. Singh F.V., Weber M., Guadagnin R.C., and Stefani H.A. Synlett (2008) 1889
50. Delmas M., Maire J.C., and Santamaria J. J. Organometal. Chem. 16 (1969) 405 and references therein
51. Nogueira C.W., Zeni G., and Rocha J.B.T. Chem. Rev. 104 (2004) 6255
52. Gilman H., Beel J.A., Brannen C.G., Bullock M.W., Dunn G.E., and Miller L.S. J. Am. Chem. Soc. 71 (1949) 1499
53. This compound has previously been characterized, see:
54. Ref. 21;
55. Tucci F.C., Chieffi A., Comasseto J.V., and Marino J.P. J. Org. Chem. 61 (1996) 4975
56. This compound has previously been characterized, see. Dabdoub M.J., Dabdoub V.B., and Guerrero Jr. P.G. Tetrahedron 53 (1997) 4199
57. Hellwinkel D., and Fahrbach G. Chem. Ber. 101 (1968) 574
58. For E-β-(trimethylstannyl)-3,4-dimethoxystyrene the alkene hydrogens give J=19.3 Hz at 6.71 and 6.84 ppm respectively. See. Koen M.J., Morgan J., Pinhey J.T., and Sherry C.J. J. Chem. Soc., Perkin Trans. 1 (1997) 487
59. This compound has previously been characterized, see: Ref. 10.
60. For E-β-(trimethylstannyl)-4-methylstyrene the alkene hydrogens give a singlet at 6.86 ppm 2H, see: Ref. 38.
61. +.
62. This compound has previously been characterized, see: Ref. 14b.
63. For (E)-4,4,5,5-tetramethyl-2-(4-methylstyryl)-1,3,2-dioxaborolane the alkene hydrogens give J=18.0 Hz at 6.10 and 7.36 ppm respectively. See. Itami K., Tonogaki K., Nokami T., Ohashi Y., and Yoshida J. Angew. Chem., Int. Ed. 45 (2006) 2404