Effect of Crown Ethers on the Regioselectivity of Allylation of Benzaldehyde with Allylic Barium Reagents

Synlett

Volumn 1997, Issue 9, 1997, Pages 1090-1092

  Yanagisawa, Akira ^a   Yamada, Yasuhiro ^a   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001882591     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1530     Document Type: Article

References (20)

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2. (b) Yanagisawa, A.; Habaue, S.; Yasue, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 6130.
3. Review: (c) Yanagisawa, A.; Yamamoto, H. In Active Metals. Preparation, Characterization, Applications; Fürstner, A., Ed.; VCH: Weinheim, Germany, 1996; p 61.
4. (a) Sell, M. S.; Rieke, R. D. Synth. Commun. 1995, 25, 4107.
5. Reviews: (b) Rieke, R. D.; Sell, M. S.; Klein, W. R.; Chen, T.-A.; Brown, J. D.; Hanson, M. V. In Active Metals. Preparation, Characterization, Applications; Fürstner, A., Ed.; VCH: Weinheim, Germany, 1996; p 1. (c) Rieke, R. D.; Hanson, M. V. Tetrahedron 1997, 53, 1925.
6. Reviews: (b) Rieke, R. D.; Sell, M. S.; Klein, W. R.; Chen, T.-A.; Brown, J. D.; Hanson, M. V. In Active Metals. Preparation, Characterization, Applications; Fürstner, A., Ed.; VCH: Weinheim, Germany, 1996; p 1. (c) Rieke, R. D.; Hanson, M. V. Tetrahedron 1997, 53, 1925.
7. 2+ is known to form a stable complex with 18-crown-6, see: (a) Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 7017. (b) Izatt, R. M.; Terry, R. E.; Haymore, B. L.; Hansen, L. D.; Dalley, N. K.; Avondet, A. G.; Christensen, J. J. J. Am. Chem. Soc. 1976, 98, 7620. (c) Takeda, Y.; Suzuki, S.; Ohyagi, Y. Chem. Lett. 1978, 1377. See also: (d) Shchori, E.; Nae, N.; Jagur-Grodzinski, J. J. Chem. Soc., Dalton Trans. 1975, 2381.
8. 2+ is known to form a stable complex with 18-crown-6, see: (a) Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 7017. (b) Izatt, R. M.; Terry, R. E.; Haymore, B. L.; Hansen, L. D.; Dalley, N. K.; Avondet, A. G.; Christensen, J. J. J. Am. Chem. Soc. 1976, 98, 7620. (c) Takeda, Y.; Suzuki, S.; Ohyagi, Y. Chem. Lett. 1978, 1377. See also: (d) Shchori, E.; Nae, N.; Jagur-Grodzinski, J. J. Chem. Soc., Dalton Trans. 1975, 2381.
9. 2+ is known to form a stable complex with 18-crown-6, see: (a) Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 7017. (b) Izatt, R. M.; Terry, R. E.; Haymore, B. L.; Hansen, L. D.; Dalley, N. K.; Avondet, A. G.; Christensen, J. J. J. Am. Chem. Soc. 1976, 98, 7620. (c) Takeda, Y.; Suzuki, S.; Ohyagi, Y. Chem. Lett. 1978, 1377. See also: (d) Shchori, E.; Nae, N.; Jagur-Grodzinski, J. J. Chem. Soc., Dalton Trans. 1975, 2381.
10. 2+ is known to form a stable complex with 18-crown-6, see: (a) Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 7017. (b) Izatt, R. M.; Terry, R. E.; Haymore, B. L.; Hansen, L. D.; Dalley, N. K.; Avondet, A. G.; Christensen, J. J. J. Am. Chem. Soc. 1976, 98, 7620. (c) Takeda, Y.; Suzuki, S.; Ohyagi, Y. Chem. Lett. 1978, 1377. See also: (d) Shchori, E.; Nae, N.; Jagur-Grodzinski, J. J. Chem. Soc., Dalton Trans. 1975, 2381.
11. Reviews: (a) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds; Pergamon Press: Oxford, 1991; Vol. 2, p 1. (b) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (c) Bach, T. Angew. Chem. Int. Ed. Engl. 1994, 33, 417. (d) Hoveyda, A. H.; Morken, J. P. Angew. Chem. Int. Ed. Engl. 1996, 35, 1262.
12. Reviews: (a) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds; Pergamon Press: Oxford, 1991; Vol. 2, p 1. (b) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (c) Bach, T. Angew. Chem. Int. Ed. Engl. 1994, 33, 417. (d) Hoveyda, A. H.; Morken, J. P. Angew. Chem. Int. Ed. Engl. 1996, 35, 1262.
13. Reviews: (a) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds; Pergamon Press: Oxford, 1991; Vol. 2, p 1. (b) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (c) Bach, T. Angew. Chem. Int. Ed. Engl. 1994, 33, 417. (d) Hoveyda, A. H.; Morken, J. P. Angew. Chem. Int. Ed. Engl. 1996, 35, 1262.
14. Reviews: (a) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds; Pergamon Press: Oxford, 1991; Vol. 2, p 1. (b) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (c) Bach, T. Angew. Chem. Int. Ed. Engl. 1994, 33, 417. (d) Hoveyda, A. H.; Morken, J. P. Angew. Chem. Int. Ed. Engl. 1996, 35, 1262.
15. (a) Dyer, R. B.; Metcalf, D. H.; Ghirardelli, R. G.; Palmer, R. A.; Holt, E. M. J. Am. Chem. Soc. 1986, 108, 3621.
16. (b) Aoki, S.; Sasaki, S.; Koga, K. Tetrahedron Lett. 1989, 30, 7229.
17. (c) Naemura, K.; Ueno, M. Bull. Chem. Soc. Jpn. 1990, 63, 3695.
18. Kaupp, M.; Schleyer, P. v. R. J. Am. Chem. Soc. 1992, 114, 491.
19. 2O (extra pure reagent, Nacalai Tesque) at 150°C for 2 h under reduced pressure (<10 Torr).
20. 24O: C, 83.55; H, 9.90. Found: C, 83.55; H, 10.10.