First Enantioselective Protonation of Prochiral Allyltrimethyltins Using Lewis Acid Assisted Chiral Brønsted Acids

Synlett

Volumn 1997, Issue 7, 1997, Pages 758-760

  Ishihara, Kazuaki ^a   Ishida, Yuji ^a   Nakamura, Shingo ^a   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542745114     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-5758     Document Type: Article

References (22)

1. (a) Hayashi, T.; Iwamura, H.; Naito, M.; Matsumoto, Y.; Uozumi, Y. J. Am. Chem. Soc. 1994, 116, 775.
2. (b) Hayashi, T.; Iwamura, H.; Uozumi, Y.; Matsumoto, Y.; Ozawa, F. Synthesis 1994, 526.
3. For recent reviews of enantioselective protonations, see: (a) Fehr, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 2566. (b) Yanagisawa, A.; Ishihara, K.; Yamamoto, H. Synlett 1997, in press.
4. For recent reviews of enantioselective protonations, see: (a) Fehr, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 2566. (b) Yanagisawa, A.; Ishihara, K.; Yamamoto, H. Synlett 1997, in press.
5. (a) Ishihara, K.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 11179.
6. (b) Ishihara, K.; Nakamura, S.; Yamamoto, H. Croat. Chem. Acta 1996, 69, 513.
7. (c) Ishihara, K.; Nakamura, S.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 12854.
8. Unfortunately, no enantioselectivity was observed in the protonation of (E)-3-phenyl-2-propenyltrimethylsilane with (R)-LBA 1 in dichloromethane (14°C, 12 h).
9. Preparation of (E)-3-phenyl-2-butenyltrialkyltin, see: Tsuji, Y.; Suzuki, T.; Watanabe, Y.; Takegami, Y. Polymer J. 1981, 13, 1099.
10. Pereyre, M.; Quintard, J.-P.; Rahm, A. "Tin in Organic Synthesis"; Butterworth & Co., Ltd. (Publishers): London, 1987; pp 131-134.
11. Dichloromethane was used as a solvent to increase the solubility of LBA at -90°C.
12. Hayashi, T.; Konishi, M.; Fukushima, M.; Mise, T.; Kagotani, M.; Tajika, M.; Kumada, M. J. Am. Chem. Soc. 1982, 104, 180.
13. Compound 6 was prepared from 2-phenyl-1-methylenecyclohexane by deprotonation (superbasic butyl lithium/potassium tert-butoxide mixture (2 equiv) in THF at -78 °C for 1 h) and subsequent stannylation (trimethyltin chloride (2.2 equiv) at -78°C; warmed to room temperature for 1 h), see: (a) Schlosser, M.; Strunk, S. Tetrahedron Lett. 1984, 25, 741. (b) Schlosser, M.; Choi, J. H.; Takagishi, S. Tetrahedron 1990, 46, 5633.
14. Compound 6 was prepared from 2-phenyl-1-methylenecyclohexane by deprotonation (superbasic butyl lithium/potassium tert-butoxide mixture (2 equiv) in THF at -78 °C for 1 h) and subsequent stannylation (trimethyltin chloride (2.2 equiv) at -78°C; warmed to room temperature for 1 h), see: (a) Schlosser, M.; Strunk, S. Tetrahedron Lett. 1984, 25, 741. (b) Schlosser, M.; Choi, J. H.; Takagishi, S. Tetrahedron 1990, 46, 5633.
15. R=20.2 min for (R)-(+)-enantiomer (minor product).
16. For preparation of 8 and 9, see: Weigand, S.; Brückner, R. Synthesis 1996, 475.
17. R=46.9 min for the acetal derived from (S)-enantiomer, see: Fujiwara, J.; Fukutani, Y.; Hasegawa, M.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004.
18. E' mechanism have been reported, see: Young, D.; Kitching, W. J. Organometal. Chem. 1983, 247, C5. (b) Kuo, C. H.; Patchett, A. A.; Wendler, N. L. J. Org. Chem. 1983, 48, 1991. (c) Jones, M.; Kitching, W. Aust. J. Chem. 1984, 37, 1863.
19. E' mechanism have been reported, see: Young, D.; Kitching, W. J. Organometal. Chem. 1983, 247, C5. (b) Kuo, C. H.; Patchett, A. A.; Wendler, N. L. J. Org. Chem. 1983, 48, 1991. (c) Jones, M.; Kitching, W. Aust. J. Chem. 1984, 37, 1863.
20. E' mechanism have been reported, see: Young, D.; Kitching, W. J. Organometal. Chem. 1983, 247, C5. (b) Kuo, C. H.; Patchett, A. A.; Wendler, N. L. J. Org. Chem. 1983, 48, 1991. (c) Jones, M.; Kitching, W. Aust. J. Chem. 1984, 37, 1863.
21. (a) Keck, G. E.; Andrus, M. B.; Castellino, S. J. Am. Chem. Soc. 1989, 111, 8136.
22. (b) Naruta, Y.; Nishigaichi, Y.; Maruyama, K. Tetrahedron 1989, 45, 1067.