Fluoride activated stereoinformation transfer from a C-Si bond of a chiral benzyl silane to C-C bonds

Tetrahedron Letters

Volumn 38, Issue 31, 1997, Pages 5429-5432

  Thayumanavan, S ^a   Park, Yong Sun ^a   Farid, Payman ^a   Beak, Peter ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORIDE; SILANE DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; DIASTEREOISOMER; STEREOCHEMISTRY; TEMPERATURE;

EID: 0030854985     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01214-8     Document Type: Article

References (27)

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20. Mills, R.J.; Taylor, N.J.; Snieckus, V. J. Org. Chem. 1989, 54, 4372. Bartoli, G.; Bosco, M.; Caretti, D.; Dalpozzo, R.; Tedesco, P.E. J. Org. Chem. 1987, 52, 4381. Kessar, S.V.; Singh, P.; Venugopal, D. J. Chem. Soc., Chem. Commun. 1985, 1258. Takano, S.; Numata, H.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1982, 769. Pilcher, A. S.; DeShong, P. J. Org. Chem. 1996, 61, 6901.
21. Mills, R.J.; Taylor, N.J.; Snieckus, V. J. Org. Chem. 1989, 54, 4372. Bartoli, G.; Bosco, M.; Caretti, D.; Dalpozzo, R.; Tedesco, P.E. J. Org. Chem. 1987, 52, 4381. Kessar, S.V.; Singh, P.; Venugopal, D. J. Chem. Soc., Chem. Commun. 1985, 1258. Takano, S.; Numata, H.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1982, 769. Pilcher, A. S.; DeShong, P. J. Org. Chem. 1996, 61, 6901.
22. Mills, R.J.; Taylor, N.J.; Snieckus, V. J. Org. Chem. 1989, 54, 4372. Bartoli, G.; Bosco, M.; Caretti, D.; Dalpozzo, R.; Tedesco, P.E. J. Org. Chem. 1987, 52, 4381. Kessar, S.V.; Singh, P.; Venugopal, D. J. Chem. Soc., Chem. Commun. 1985, 1258. Takano, S.; Numata, H.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1982, 769. Pilcher, A. S.; DeShong, P. J. Org. Chem. 1996, 61, 6901.
23. 2d,10
24. Thayumanavan, S.; Basu, A.; Beak, P. J. Am. Chem. Soc. 1997, 119, 0000.
25. The diastereomer 4a is the non-polar diastereomer and 4b is the polar diastereomer, as eluted in the CSP-HPLC.
26. Clayden, J.; Pink, J. H. Tetrahedron Lett. 1997, 38, 2565.
27. Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552.