Stereoselective cyclopropylmethylation reactions of homoallylstannanes with carbon electrophiles

Tetrahedron

Volumn 56, Issue 27, 2000, Pages 4683-4689

  Sugawara, Masanobu ^a   Yoshida, Jun Ichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Cyclopropylmethylation; Homoallylstannane; Stereoselective; ; elimination

Indexed keywords

ACETAL; ALDEHYDE; CARBON; CHLORIDE; TIN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; METHYLATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0034733739     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00389-6     Document Type: Article

References (32)

1. (a) Fleming, I. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds; Pergamon Press: Oxford, 1991; Vol. 2, p 563.
2. (b) Pereyre, M.; Quintard, J.-B.; Rahm, A. Tin in Organic Synthesis; Butterworth & Co.: London, 1987.
3. (c) Davies, A. G. Organotin Chemistry; VCH: Weinheim, 1997.
4. (d) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
5. (e) Nishigaichi, Y.; Takuwa, A. Tetrahedron 1993, 49, 7395.
6. For example, Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Synthesis; Wiley: New York, 1995; p 240.
7. Reactions of homoallylstannanes with hetero electrophiles have been reported. (a) Peterson, D. J.; Robbins, M. D. Tetrahedron Lett. 1972, 2135. (b) Paterson, D. J.; Robbins, M. D.; Hansen, J. R. J. Organomet. Chem. 1974, 73, 237. (c) Nicolaou, K. C.; Claremon, D. A.; Barnette, W. E.; Seitz, S. P. J. Am. Chem. Soc. 1979, 101, 3704. (d) Ueno, Y.; Ohta, M.; Okawara, M. Tetrahedron Lett. 1982, 23, 2577. (e) Herndon, J. W.; Harp, J. J. Tetrahedron Lett. 1992, 33, 6243.
8. Reactions of homoallylstannanes with hetero electrophiles have been reported. (a) Peterson, D. J.; Robbins, M. D. Tetrahedron Lett. 1972, 2135. (b) Paterson, D. J.; Robbins, M. D.; Hansen, J. R. J. Organomet. Chem. 1974, 73, 237. (c) Nicolaou, K. C.; Claremon, D. A.; Barnette, W. E.; Seitz, S. P. J. Am. Chem. Soc. 1979, 101, 3704. (d) Ueno, Y.; Ohta, M.; Okawara, M. Tetrahedron Lett. 1982, 23, 2577. (e) Herndon, J. W.; Harp, J. J. Tetrahedron Lett. 1992, 33, 6243.
9. Reactions of homoallylstannanes with hetero electrophiles have been reported. (a) Peterson, D. J.; Robbins, M. D. Tetrahedron Lett. 1972, 2135. (b) Paterson, D. J.; Robbins, M. D.; Hansen, J. R. J. Organomet. Chem. 1974, 73, 237. (c) Nicolaou, K. C.; Claremon, D. A.; Barnette, W. E.; Seitz, S. P. J. Am. Chem. Soc. 1979, 101, 3704. (d) Ueno, Y.; Ohta, M.; Okawara, M. Tetrahedron Lett. 1982, 23, 2577. (e) Herndon, J. W.; Harp, J. J. Tetrahedron Lett. 1992, 33, 6243.
10. Reactions of homoallylstannanes with hetero electrophiles have been reported. (a) Peterson, D. J.; Robbins, M. D. Tetrahedron Lett. 1972, 2135. (b) Paterson, D. J.; Robbins, M. D.; Hansen, J. R. J. Organomet. Chem. 1974, 73, 237. (c) Nicolaou, K. C.; Claremon, D. A.; Barnette, W. E.; Seitz, S. P. J. Am. Chem. Soc. 1979, 101, 3704. (d) Ueno, Y.; Ohta, M.; Okawara, M. Tetrahedron Lett. 1982, 23, 2577. (e) Herndon, J. W.; Harp, J. J. Tetrahedron Lett. 1992, 33, 6243.
11. Reactions of homoallylstannanes with hetero electrophiles have been reported. (a) Peterson, D. J.; Robbins, M. D. Tetrahedron Lett. 1972, 2135. (b) Paterson, D. J.; Robbins, M. D.; Hansen, J. R. J. Organomet. Chem. 1974, 73, 237. (c) Nicolaou, K. C.; Claremon, D. A.; Barnette, W. E.; Seitz, S. P. J. Am. Chem. Soc. 1979, 101, 3704. (d) Ueno, Y.; Ohta, M.; Okawara, M. Tetrahedron Lett. 1982, 23, 2577. (e) Herndon, J. W.; Harp, J. J. Tetrahedron Lett. 1992, 33, 6243.
12. (a) Sugawara, M.; Yoshida, J. J. Am. Chem. Soc. 1997, 119, 11986.
13. (b) Sugawara, M.; Yoshida, J. Synlett. 1998, 1057.
14. (c) Sugawara, M.; Yoshida, J. Tetrahedron Lett. 1999, 40, 1717 and references cited therein.
15. It has been reported that homoallysilanes reacted with acid chlorides to give the corresponding cyclopropylmethyl ketones. Intermolecular reaction (a) Sakurai, H.; Imai, T.; Hosomi, A Tetrahedron Lett. 1977, 4045. Intramolecular reaction. (b) Hatanaka, Y.; Kuwajima, I. Tetrahedron Lett. 1986, 27, 719.
16. It has been reported that homoallysilanes reacted with acid chlorides to give the corresponding cyclopropylmethyl ketones. Intermolecular reaction (a) Sakurai, H.; Imai, T.; Hosomi, A Tetrahedron Lett. 1977, 4045. Intramolecular reaction. (b) Hatanaka, Y.; Kuwajima, I. Tetrahedron Lett. 1986, 27, 719.
17. Jerkunica J.M., Traylor T.G. J. Am. Chem. Soc. 93:1971;6278.
18. Sugawara M., Yoshida J. Chem. Commun. 1999;505.
19. Low temperature (-75°C) generation of the Grignard reagent from cyclopropylmethyl bromide and its reaction with an electrophile leads to predominant formation of cyclopropylmethylated product: Kundig, E. P.; Perret, C. Helv. Chim. Acta 1981, 64, 2606. See also references cited therein.
20. Seyferth D., Weiner M.A. J. Am. Chem. Soc. 84:1962;361.
21. Tsunoda T., Suzuki M., Noyori R. Tetrahedron Lett. 21:1980;71.
22. Lambert, J.B.; Zhao, Y.; Emblide, R.W.; Salvador, L.A.; Liu, X.; So, J.-H.; Chelius, E.C. Acc. Chem. Res. 1999, 32, 183 and references cited therein. See also Ref. 4a.
23. The erythro stereochemistry was determined by comparison with an authentic sample, which was prepared by the cyclopropanation by a zinc carbenoid of the corresponding erythro homoallylalcohol. cf. Yamamoto, Y.; Yatagai, H.; Naruta, Y.; Maruyama, K. J. Am. Chem. Soc. 1980, 102, 7107.
24. (a) Yamamoto, Y.; Yatagai, H.; Naruta, Y.; Maruyama, K. J. Am. Chem. Soc. 1980, 102, 7109.
25. See also (b) Keck, G. E.; Abbott, D. E.; Boden, E. P.; Enholm, E. J. Tetrahedron Lett. 1984, 25, 3927.
26. (a) Keck, G. E.; Kenneth, A. S.; Cressman, E. N. K.; Abbott, D. E. J. Org. Chem. 1994, 59, 7889.
27. See also, (b) Keck, G. E.; Dougherty, S. M.; Savin, K. A. J. Am. Chem. Soc. 1995, 117, 6210.
28. (c) Denmark, S. E.; Weber, E. J. J. Am. Chem. Soc. 1994, 106, 7970.
29. (d) Nishigaichi, Y.; Takuwa, A. Tetrahedron Lett. 1999, 40, 109.
30. Similar stereoselectivities were observed in the reactions of allylsilanes with aldehydes in the presence of a Lewis acid. Hayashi, T.; Kabeta, K.; Hamachi, I.; Kumada, M. Tetrahedron Lett. 1983, 24, 2865. See also, Santelli, M.; Pons, J.-M. Lewis Acids and Selectivity in Organic Synthesis; CRC Press: Boca Raton, 1996; p 91.
31. Similar stereoselectivities were observed in the reactions of allylsilanes with aldehydes in the presence of a Lewis acid. Hayashi, T.; Kabeta, K.; Hamachi, I.; Kumada, M. Tetrahedron Lett. 1983, 24, 2865. See also, Santelli, M.; Pons, J.-M. Lewis Acids and Selectivity in Organic Synthesis; CRC Press: Boca Raton, 1996; p 91.
32. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, Jr., J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. GAUSSIAN 98; Revision A.7, Gaussian, Inc.: Pittsburgh, PA, 1998.