Asymmetric synthesis of 2°- and 3°-carbinols via B-methallyl-10-(TMS and Ph)-9-borabicyclo[3.3.2]decanes

Journal of Organic Chemistry

Volumn 72, Issue 25, 2007, Pages 9772-9775

  Román, José G ^a   Soderquist, John A ^a  

^a UNIVERSITY OF PUERTO RICO   (Puerto Rico)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; ENANTIOMERS; KETONES; SYNTHESIS (CHEMICAL);

CARBINOLS; HOMOALLYLIC ALCOHOLS; METHALLYLBORANES;

PARAFFINS;

ALCOHOL DERIVATIVE; ALDEHYDE; ALLYL COMPOUND; BICYCLO COMPOUND; BORANE DERIVATIVE; DECANE; KETONE DERIVATIVE; METHANOL DERIVATIVE; REAGENT;

ADDITION REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; ENANTIOMER; GRIGNARD REACTION; PRECURSOR; PURIFICATION;

BICYCLO COMPOUNDS; BORON COMPOUNDS; METHANOL; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 36849009170     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701633k     Document Type: Article

References (48)

1. (a) Herold, T.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1978, 17, 768.
2. (b) Herold, T.; Schrott, C.; Hoffmann, R. W. Chem. Ber. 1981, 114, 359.
3. (c) Hoffmann, R. W.; Herold, T. Chem. Ber. 1981, 114, 375.
4. (d) Brown, H. C.; Jadhav, P. K.; Perumal, P. T. Tetrahedron Lett. 1984, 25, 5111-5114.
5. (e) Brown, H. C.; Jadhav, P. K.; Perumal, P. T. J. Org. Chem. 198,6, 51, 432.
6. (f) Masamune, S.; Short, R. P. J. Am. Chem. Soc. 1989, 111, 1892.
7. See also: (g) Ramachandran, P. V. Aldrichim. Acta 2002, 35, 23 and references cited therein,
8. (h) Flamme, E. M.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 13644.
9. (i) Yakelis, N. A.; Roush, W. R. J. Org. Chem. 2003, 68, 3838.
10. (j) Gao, X.; Hall, D. G. J. Am. Chem. Soc. 2003, 125, 9308.
11. (k) Morgan, J. B.; Morken, J. P. Org. Lett. 2003, 5, 2573.
12. (l) Barrett, A. G. M.; Braddock, D. C.; de Koning, P. D.; White, A. J. P.; Williams, D. J. J. Org. Chem. 2000, 65, 375.
13. (m) Barrett, A. G. M.; Beall, J. C.; Braddock, D. C.; Flack, K.; Gibson, V. C.; Salter, M. M. J. Org. Chem. 2000, 65, 6508.
14. (n) Corey, E. J.; Yu, C.; Kim, S. S. J. Am. Chem. Soc. 1989, 111, 5495.
15. (o) Brown, H. C.; Racherla, U. S.; Liao, Y.; Khanna, V. V. J. Org. Chem. 1992, 57, 6608.
16. (a) Wu, T. R.; Shen, L.; Chong, J. M. Org. Lett. 2004, 6, 2701.
17. (b) Keck, G. E.; Krishnamurthy, D. Org. Synth. 1998, 75, 12.
18. (c) Yamamoto, H.; Ishiba, A.; Nakashima, H.; Yanagisawa, A. J. Am. Chem. Soc. 1996, 118, 4723.
19. (d) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.
20. (e) Loh, T.-P.; Zhou, J. R.; Li, X. R. Tetrahedron Lett. 1999, 40, 9333.
21. (f) Pu, L.; Yu, H.-B. Chem. Rev. 2001, 101, 757.
22. (g) Pu, L. Tetrahedron 2003, 59, 9873.
23. (h) Denmark, S. E.; Fu, J. Chem. Rev. 2003, 103, 2763.
24. (a) Walsh, P. J.; Kim, J. G.; Camp, E. H. Org. Lett. 2006, 7, 4413.
25. See also: (b) Källström, S.; Jagt, R. B.; Sillanpää, R.; Feringa, B. L.; Minnaard, A. J.; Leino, R. Eur. J. Org. Chem. 2006, 3826.
26. (a) Nelson, S. G.; Cheung, S. W.; Kassick, A. J.; Hilfiker, M. A. J. Am. Chem. Soc. 2002, 124, 13654.
27. (b) De Brabander, J. K.; Garcia-Fortanet, J.; Jiang, X. J. Am. Chem. Soc. 2005, 127, 11254.
28. (c) Nakada, M.; Suzuki, T.; Inoue, M. J. Am. Chem. Soc. 2003, 125, 1140.
29. (a) Burgos, C. H.; Canales, E.; Matos, K.; Soderquist, J. A. J. Am. Chem. Soc. 2005, 127, 8044.
30. (b) Available from Sigma-Aldrich, Inc.
31. Canales, E.; Prasad, G.; Soderquist, J. A. J. Am. Chem. Soc. 2005, 127, 11572.
32. Alexakis, A.; Mutti, S.; Mangeney, P. J. Org. Chem. 1992, 57, 1224.
33. (a) Nicolaou, K. C.; Van Delf, F. L.; Mitchel, H. J.; Rodríguez, R. M.; Rudsan, F. Angew. Chem., Int. Ed. Engl. 1999, 37, 1871.
34. (b) Schmidt, U.; Schmidt, J. Synthesis 1994, 300.
35. (c) Ciufolini, M. A.; Hermann, C. W.; Whitmire, K. H.; Byrne, N. E. J. Am. Chem. Soc. 1989, 111, 3473.
36. For a recent review see: Felpin, F.-X.; Lebreton, J. Eur. J. Org. Chem. 2003, 3693.
37. (a) Itsuno, S.; Watanabe, K.; Koichi, I.; El-Shehawy, A.; Sarhan, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 109.
38. (b) Wantanabe, K.; Ito, K.; Itsuno, S. Tetrahedron; Asymmetry 1995, 6, 1531.
39. (c) Wantanabe, K.; Kuroda, S.; Yokoi, A.: Ito, K; Itsuno, S. J. Organomet. Chem. 1999, 581, 103.
40. Brown, H. C.; Chen, G. M.; Ramachandran, P. V. Angew. Chem., Int. Ed. 1999, 38, 825.
41. (a) Hernandez, E.; Canales, E.; Gonzalez, E.; Soderquist, J. A. Pure Appl. Chem .2006, 78, 1389.
42. (b) Hernandez, E.; Canales, E.; Soderquist, J. A. J. Am. Chem. Soc 2006, 128, 8712.
43. See also: (c) Gonzalez, A. Z.; Soderquist, J. A. Org. Lett. 2007, 9, 1081.
44. (a) Paterson, I.; Goodman, J. M. Tetrahedron Lett. 1989, 30, 997.
45. (b) Matsumoto, Y.; Hayashi, T.; Ito, Y. Tetrahedron 1994, 50, 335.
46. (a) Masamune, S.; Hirama, M.; Mori, S.; Ali, Sk. A.; Garvey, D. S. J. Am. Chem. Soc 1981, 103, 1568.
47. (b) Nicolaou, K. C.; Daines, R. A.; Chakraborty, T. K; Ogawa, T.; Papahatjis, D. P.; Uenishi, J J. Am. Chem. Soc. 1988, 110, 4660.
48. (c) Nicolaou, K. C.; Daines, R. A.; Chakraborty, T. K; Ogawa J. Am. Chem. Soc. 1988, 110, 4685.