Intramolecular hydrogen bond-promoted C-C bond formation: Reaction rate enhancement and regioselective allylation of carbonyl compounds

Chemical Communications

Volumn , Issue 22, 1998, Pages 2443-2444

  Ito, Hajime ^a   Ujita, Yasuaki ^a   Tateiwa, Jun Ichi ^a   Sonoda, Motohiro ^a   Hosomi, Akira ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; CARBONYL DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION KINETICS; HYDROGEN BOND;

EID: 0032556386     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a807172a     Document Type: Article

References (19)

1. S. Shambayati and S. L. Schreiber, in Comprehensive Organic Synthesis, ed. B. M. Trost, Pergamon, Oxford, 1991, vol. 1, pp. 283-353.
2. A. Hosomi and H. Sakurai, Tetrahedron Lett., 1976, 1295.
3. S, Castellino and D. E. Volk, in Encyclopedia of Reagents for Organic Synthesis, ed. L. A. Paquette, Wiley, 1995, vol. 1, pp. 125-128;
4. Y. Yamamoto and N. Asao, Chem. Rev., 1993, 2207.
5. V. Gevorgyan, I. Kadota and Y. Yamamoto, Tetrahedron Lett., 1993, 34, 1313;
6. S. E. Denmark, E. J. Weber, T. M. Wilson and T. M. Willson, Tetrahedron Lett., 1989, 45, 1053;
7. A. Yanagisawa, M. Morodome, H. Nakashima and H. Yamamoto, Synlett, 1997, 1309:
8. G. Kaur, K. Manju and S. Trehan, Chem. Commun., 1996, 581.
9. T. M. Cokley, P. J. Harvey, R. L. Marshall, A. McCluskey and D. J. Young, J. Org. Chem., 1997, 62, 1961;
10. T. M. Cokley, R. L. Marshall, A. McCluskey and D. J. Young, Tetrahedron Lett. 1996, 37, 1905;
11. N. Asao, A. Noriko, Z. Tan and K. Maruoka, Synlett, 1998, 377.
12. After the submission of our paper, condensation reactions between more reactive tetraallyltin species and salicylaldehyde were reported. M. Yasuda, T. Fujibayashi and A. Baba, J. Org. Chem., 1998, 63, 6401.
13. W. W. Cleland and M. M. Kreevoy, Science, 1994, 264, 1887;
14. G. A. Kumar and M. A. McAllister, J. Am. Chem. Soc., 1998, 120, 3159;
15. E. L. Ash, J. L. Sudmeier, E. C. D. Fabo and W. W. Bachovchin, Science, 1997, 278, 1128.
16. 3) 0.86 (t, J 7.3, 9H), 1.20-1.65 (m, 18H), 8.18 (d, J 9.2, 1H), 8.20 (d, J 9.2, 3.0, 1H), 8.54 (d, J 3.0, 1H), 10.28 (s, 1H).
17. A reaction between A and allyltributyltin (1.3 equiv.) in THF for 48 h gave 3c (11%) and le (82%) at room temperature.
18. S. J. Angyal, P. J. Morris, J. R. Tetaz and J. G. Wilson, J. Chem. Soc., 1950, 2141.
19. Similar selectivity was achieved using a Lewis acid catalyst. T. Ooi, D. Uraguchi, N. Kagoshima and M. Maruoka, J. Am. Chem. Soc., 1998, 120, 5327.