Homologation and alkylation of boronic esters and boranes by 1,2-metallate rearrangement of boron ate complexes

Chemical Record

Volumn 9, Issue 1, 2009, Pages 24-39

  Thomas, Stephen P ^a,b   French, Rosalind M ^a,c   Jheengut, Vishal ^a   Aggarwal, Varinder K ^a,c  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b UNIVERSITY OF BASEL   (Switzerland)

^c University of Bristol ^*  (United Kingdom)

Author keywords

1,2 metallate rearrangement; Boronic ester; Chiral carbanions; Homologation; Lithiated carbamates; Sulfur ylides

Indexed keywords

BORANE DERIVATIVE; CARBAMIC ACID DERIVATIVE; CHLORIDE; ESTER; LITHIUM; SULFUR DERIVATIVE; ZINC CHLORIDE; ZINC DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

ALKYLATION; BORANES; CARBAMATES; CHLORIDES; ESTERS; LITHIUM; MOLECULAR STRUCTURE; STEREOISOMERISM; SULFUR COMPOUNDS; ZINC COMPOUNDS;

EID: 61349161740     PISSN: 15278999     EISSN: 15280691     Source Type: Journal    
DOI: 10.1002/tcr.20168     Document Type: Article

References (59)

1. (a) Brown, H. C.; Singaram, B. Pure Appl Chem 1987, 59, 879;
2. (b) Pelter, A.; Smith, K.; Brown, H. C. Borane Reagents; Academic Press: New York, 1988;
3. (c) Kaufmann, D. E.; Matteson, D. S., Eds. Science of Synthesis; Vol. 6, Boron Compounds; Georg Thieme Verlag; Stuttgart-New York, 2004;
4. (d) Matteson, D. S. Stereodirected Synthesis with Organoboranes; Springer: New York, 1995, pp. 162-220;
5. (e) Crudden, C. M.; Edwards, D. Eur J Org Chem 2003, 2003, 4695-4712;
6. (f) Hall D. G. In Boronic Acids. Hall, D. G., Ed. Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2005, pp. 1-85.
7. (a) Brown, H. C.; Zweifel, G. J Am Chem Soc 1961, 83, 486;
8. (b) Zweifel, G.; Brown, H. C. J Am Chem Soc 1964, 86, 4393.
9. (a) Matteson, D. S.; Ray, R. J Am Chem Soc 1980, 102, 7590-7591;
10. (b) Matteson, D. S.; Ray, R.; Rocks, R. R.; Tsai, D. J. S. Organometallics 1983, 2, 1536-1543.
11. (c) Matteson, D. S.; Sadhu, K. M. J Am Chem Soc 1983, 105, 2077-2078.
12. (a) Matteson D. S. Chem Rev 1989, 89, 1535;
13. (b) Matteson D.S. Tetrahedron 1989, 45, 1859;
14. (c) Matteson, D. S. Boronic Acids. Hall, D. G., Ed. Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2005, pp. 305-342;
15. (d) Matteson, D. S. Acc Chem Res 1988, 21, 294-300;
16. (e) Matteson, D. S. Chem Rev 1989, 89, 1535-1551;
17. (f) Matteson, D. S. Tetrahedron 1989, 45, 1859-1885;
18. (g) Matteson, D. S. Pure Appl Chem 1991, 63, 339-44;
19. (h) Matteson, D. S. Tetrahedron 1998, 54, 10555-10607;
20. (i) Matteson, D. S. Chem Tech 1999, 29, 6-14.
21. Corey, E. J.; Barnes-Seeman, D.; Lee, T. W. Tetrahedron: Asymmetry 1997, 8, 3711-3713.
22. Midland, M. M. J Org Chem 1998, 63, 914-915.
23. Tsai, D. J. S.; Jesthi, P. K.; Matteson, D. S. Organometallics 1983, 2, 1543-1545.
24. Hiscox, W. C.; Matteson, D. S. J Organomet Chem 2000, 614-615, 314-317.
25. Matteson, D. S.; Man, H.-W.; Ho, O. C. J Am Chem Soc 1996, 118, 4560-4566.
26. (a) Ditrich, K.; Bube, T.; Stürmer, R.; Hoffmann, R. W. Angew Chem Int Ed Eng 1986, 25, 1028-1030;
27. (b) Hoffmann, R. W.; Ditrich, K; Köster, G. Stürmer, R. Chem Ber 1989, 122, 1783-1789;
28. (c) Stürmer, R.; Hoffmann, R. W. Chem Ber 1994, 127, 2511-2518;
29. (d) Stürmer, R.; Hoffmann, R. W. Chem Ber 1994, 127, 2519-2526.
30. Maurer, K. W.; Armstrong, R. W. J Org Chem 1996, 61, 3106-3116.
31. (a) Davoli, P.; Spaggiari, A.; Castagnetti, L.; Prati, F. Org Biomol Chem 2004, 2, 38-47;
32. (b) Davoli, P.; Fava, R.; Morandi, S.; Spaggiari, A.; Prati, F. Tetrahedron 2005, 61, 4427-4436.
33. Tripathy, P. B.; Matteson, D. S. Synthesis 1990, 200-206.
34. Matteson, D. S.; Man, H. W. J Org Chem 1996, 61, 6047-6051.
35. Matteson, D. S.; Hurst, G. D. Heteroat Chem 1990, 1, 65-74.
36. Aggarwal, V. K.; Harvey, J. N; Robiette, R. Angew Chem Int Ed 2005, 44, 5468-5471.
37. (a) Aggarwal, V. K.; Winn, C. L. Acc Chem Res 2004, 38, 611;
38. (b) McGarrigle, E. M.; Myers, E. L.; Illa, O.; Shaw, M. A.; Riches, S. L.; Aggarwal, V. K. Chem Rev 2007, 107, 5841-5883.
39. Aggarwal, V. K.; Fang, G. Y.; Schmidt, A. T. J Am Chem Soc 2005, 127, 1642-1643.
40. Fang, G. Y.; Wallner, O. A.; Blasio, N. Di; Ginesta, X.; Harvey, J. N.; Aggarwal, V. K. J Am Chem Soc 2007, 129, 14632-14639.
41. Fang, G. Y.; Aggarwal, V. K. Angew Chem Int Ed 2007, 46, 359-362.
42. Hoffmann, R. W. Chem Rev 1989, 89, 1841.
43. Howells, D.; Robiette, R.; Fang, G. Y.; Knowles, S. L.; Woodrow, M. D.; Harvey, J. N.; Aggarwal, V. K. Org Biomol Chem 2008, 6, 1185-1189.
44. Bottoni, A.; Lombardo, M.; Neri, A.; Trombini, C. J Org Chem 2003, 68, 3397-3405.
45. Hoffmann, R. W.; Nell, P. G.; Leo, R.; Harms, K. Chem Eur J 2000, 6, 3359-3365.
46. Blakemore, P. R.; Marsden, S. P.; Vater, H. D. Org Lett 2006, 8, 773-776.
47. Blakemore, P. R.; Bürge, M. S. J Am Chem Soc 2007, 129, 3068-3069.
48. Vigneron, J. P.; Dhaenens, M; Horeau, A. Tetrahedron 1973, 29, 1055-1059.
49. (a) Beckmann, E.; Desai, V.; Hoppe, D. Synlett 2004, 2275-2280;
50. (b) Beckmann, E.; Hoppe, D. Synthesis 2005, 217-222.
51. Besong, G.; Jarowicki, K.; Kocienski, P. J.; Sliwinski, E.; Boyle, F. T. Org Biomol Chem 2006, 4, 2193-2207.
52. Stymiest, J. L.; Dutheuil, G.; Mahmood, A.; Aggarwal, V. K. Angew Chem Int Ed 2007, 46, 7491-7494.
53. O'Brien, P.; Bilke, J. L. Angew Chem Int Ed 2008, 47, 2734-2736.
54. Aggarwal, V. K.; Fang, G. Y.; Ginesta, X.; Howells, D. M.; Zaja, M. Pure App Chem 2006, 78, 215-229.
55. (a) Dearden, M. J.; Firkin, C, R.; Hermet, J. -P. R.; O'Brien, P. J Am Chem Soc 2002, 124, 11870;
56. (b) Dixon, A. J.; McGrath, M. J.; O'Brien, P. Org Synth 2006, 83, 141.
57. McGrath, M. J.; O'Brien, P. Synthesis 2006, 2233-2241.
58. Coldham, I.; Patel, J. J.; Raimbault, S.; Whittaker, D. T. E.; Adams, H.; Fang, G. Y.; Aggarwal, V. K. Org Lett 2008, 10, 141-143.
59. Matteson, D. S. Med Res Rev 2008, 28, 233-246.