Indium-Mediated Reaction of Trialkylsilyl Propargyl Bromide with Aldehydes: Highly Regioselective Synthesis of Allenic and Homopropargylic Alcohols

Journal of the American Chemical Society

Volumn 125, Issue 43, 2003, Pages 13042-13043

  Lin, Man Jing ^a   Loh, Teck Peng ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; BROMINE DERIVATIVE; INDIUM; ORGANIC SOLVENT;

AQUEOUS SOLUTION; ARTICLE; COMPLEX FORMATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0142183441     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja037410i     Document Type: Article

References (22)

1. For reviews, see: (a) Yamamoto, H. In Comprehensive Organic Synthesis; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; Vol, 2, Chapter 1.3, pp 81-98,
2. (b) Panek, J. S. In Comprehensive Organic Synthesis; Schreiber, S. L., Ed.; Pergamon: Oxford, 1991, Vol. 1, p 595 and references therein.
3. (a) Miao, W.; Chan, T. H. Synthesis 2003, 5, 785.
4. (b) Reddy, L. R.; Gais, H. J.; Woo, C. W.; Raabe, G. J. Am. Chem. Soc. 2002, 124, 10427.
5. (c) Evans, D. A.; Sweeney, Z. K.; Rovis, T.; Tedrow, J. S. J. Am. Chem. Soc. 2001, 123, 12095.
6. (d) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199.
7. (e) Marshall, J. A.; Adams, N. D. J. Org. Chem. 1999, 64, 5201.
8. (f) Ogoshi, S.; Fukunishi, Y.; Tsutsumi, K.; Kurosawa, H. Chem. Commun. 1995, 2485.
9. (g) Doherty, S.; Corrigan, J. F.; Carty, A. J.; Sappa, E. Adv. Organoment. Chem. 1995, 37, 39.
10. (h) Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589.
11. (i) Hoffmann, R. W.; Lanz, J.; Metternich, R.; Tarava, G.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1987, 26, 1145.
12. (j) Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579.
13. (a) Isaac, M. B.; Chan, T. H. Chem. Commun. 1995, 1003.
14. (b) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225.
15. Yi, X. H.; Meng, Y.; Hua, X. G.; Li, C. J. J. Org. Chem. 1998, 63, 7472.
16. Loh, T. P.; Xu, K. C.; Ho, D. S. C.; Sim, K. Y. Synlett 1998, 4, 369.
17. Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3229.
18. Nokami, J.; Tamaoka, T.; Koguchi, T.; Okawara, R. Chem. Lett. 1984, 1939.
19. Hammond, G. B.; Wang, Z. G. J. Org. Chem. 2000, 65, 6547.
20. (a) Hershberg, E. B.; Oliveto, E. P.; Gerold, C.; Johnson, L. Am. J. Chem. Soc. 1951, 73, 5073.
21. (b) Loh T. P.; Hu, Q. Y.; Chok, Y. K.; Tan, K. T. Tetrahedron Lett. 2001, 42, 9277.
22. Kondo, T.; Kodoi, K.; Nishinaga, E.; Okada, T.; Morisaki, Y.; Watanabe, Y.; Mitsudo, T. J. Am. Chem. Soc. 1998, 120, 5587.