Bidirectional asymmetric allylboration. A convenient asymmetric synthesis of C2-symmetric 3-methylenepentane-1,5-diols and rapid access to C2-symmetric spiroketals

Journal of Organic Chemistry

Volumn 65, Issue 2, 2000, Pages 375-380

  Barrett, Anthony G M ^a   Braddock, D Christopher ^a   De Koning, Pieter D ^a   White, Andrew J P ^a   Williams, David J ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CRYSTAL STRUCTURE; MOLECULAR INTERACTION; SYNTHESIS; UNITED KINGDOM;

EID: 0034723399     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991205x     Document Type: Article

References (42)

1. Alonso, F.; Lorenzo, E.; Yus, M. Tetrahedron Lett. 1997, 38, 2187.
2. (a) Bates, R. B.; Beavers, W. A.; Gordon, B. J. Org. Chem. 1979, 44, 3800,
3. (b) Klein, J.; Medlik-Balan, A.; Meyer, A. Y.; Chorev, M. Tetrahedron 1976, 32, 1839.
4. (c) Bubnov, Y. N.; Gurskii, M. E.; Pershin, D. G. Bull. Acad. Sci., USSR, Div. Chem. Sci. 1987, 36, 1107.
5. (d) Imai, T.; Nishida, S. Synthesis 1993, 395.
6. (e) Gómez, C.; Ramón, D. J.; Yus, M. Tetrahedron 1993, 49, 4117.
7. (f) Kang, S.-K.; Park, D.-C.; Park, C.-H.; Jang, S.-B. Synth. Commun. 1995, 25, 1359.
8. (g) Majetich, G.; Nishidie, H.; Zhang, Y. J. Chem. Soc., Perkin Trans. 1 1995, 453.
9. (h) Li, C.-J. Tetrahedron Lett. 1995, 36, 517.
10. (i) Masuyama, Y.; Kagawa, M.; Kurusu, Y. Chem. Commun. 1996, 1585.
11. (j) Krief, A.; Dumont, W. Tetrahedron Lett. 1997, 38, 657 and references therein.
12. (a) Brown, H. C.; Jadhav, P. K. J. Am. Chem. Soc. 1983, 105, 2092.
13. (b) Roush, W. R. Allyl Organometallics. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: New York, 1991; Vol. 2, pp 1-53 and references therein.
14. (c) Barrett, A. G. M.; Wan, P. W. H. J. Org. Chem. 1996, 61, 8667 and references therein.
15. Barrett, A. G. M.; Braddock, D. C.; de Koning, P. D. Chem. Commun. 1999, 459.
16. Bahl, J. J.; Bates, R. B.; Beavers, W. A.; Mills, N. S. J. Org. Chem. 1976, 41, 1620.
17. Brown, H. C.; Jadhav, P. K.; Perumal, P. T. Tetrahedron Lett. 1984, 25, 5111.
18. Racherla, U. S.; Brown, H. C. J. Org. Chem. 1991, 56, 401.
19. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
20. Annunziata, R.; Cinquini, M.; Cozzi, F.; Restelli, A. J. Chem. Soc., Perkin Trans, 1 1985, 2293.
21. (a) Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Soc., Chem. Commun. 1981, 465.
22. (b) Bongini, A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Org. Chem. 1982, 47, 4626.
23. (c) Bartlett, P. A.; Meadows, J. D.; Brown, E. G.; Morimoto, A.; Jernstedt, K. K. J. Org. Chem. 1982, 47, 4013.
24. Duan, J. J.-W.; Smith, A. B. J. Org. Chem. 1993, 58, 3703.
25. Perron, F.; Albizati, K. F. Chem. Rev. 1989, 89, 1617.
26. (a) Mori, K.; Uematsu, T.; Watanabe, H.; Yanagi, K.; Minobe, M. Tetrahedron Lett. 1984, 25, 3875.
27. (b) Mori, K.; Uematsu, T.; Yanagi, K.; Minobe, M. Tetrahedron 1985, 41, 2751.
28. (a) Danieli, B.; Lesma, G.; Palmisano, G.; Tollari, S. J. Chem. Soc., Perkin Trans. 1 1984, 1237.
29. (b) Adamczyk, M.; Reddy, R. E. Tetrahedron 1996, 52, 14688.
30. (a) Pettit, G. R. Pure Appl. Chem. 1994, 66, 2271.
31. (b) Pettit, G. R.; Cichacz, Z. A.; Gao, F.; Herald, C. L.; Boyd, M. R.; Schmidt, J. M.; Hooper, J. N. A. J. Org. Chem. 1993, 58, 1302.
32. (c) Fumtani, N.; Shinoda, K.; Matsunaga, S. J. Am. Chem. Soc. 1993, 115, 3977.
33. Pietruszka, J. Angew. Chem., Int. Ed. Engl. 1998, 37, 2629.
34. (a) Evans, D. A.; Coleman, P. J.; Dias, L. C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2737.
35. (b) Evans, D. A.; Trotter, B. W.; Côté, B.; Coleman, P. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 2741.
36. (c) Evans, D. A.; Trotter, B. W.; Côté, B.; Coleman, P. J.; Dias, L. C.; Tyler, A. N. Angew. Chem., Int. Ed. Engl. 1997, 36, 2744.
37. (d) Guo, J.; Duffy, K. J.; Stevens, K. L.; Dalko, P. I.; Roth, R. M.; Kayward, M. M.; Kishi, Y. Angew. Chem., Int. Ed. Engl. 1998, 37, 187.
38. (e) Hayward, M. M.; Roth, R. M.; Duffy, K. J.; Dalko, P. I.; Stevens, K. L.; Guo, J.; Kishi, Y. Angew. Chem., Int. Ed. Engl. 1998, 37, 190.
39. Paquette, L. A.; Zuev, D. Tetrahedron Lett. 1997, 38, 5115.
40. Claffey, M. M.; Heathcock, C. H. J. Org. Chem. 1996, 61, 7646.
41. Menges, M.; Brückner, R. Liebigs Ann. 1995, 365.
42. Schmid, C. R.; Bryant, J. D. Org. Synth. 1993, 72, 6.