2,6-bis[(2S)-tetrahydrofuran-2-yl]phenyl diselenide: An effective reagent for asymmetric electrophilic addition reactions to olefins

Tetrahedron Letters

Volumn 38, Issue 27, 1997, Pages 4753-4756

  Déziel, Robert ^a   Malenfant, Eric ^a   Thibault, Carl ^a   Fréchette, Sylvie ^a   Gravel, Michel ^a  

^a BOEHRINGER INGELHEIM CANADA LTD   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOSELENIUM DERIVATIVE; REAGENT;

ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0039696469     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01030-7     Document Type: Article

References (12)

1. (a) Déziel, R.; Malenfant, E.; Bélanger, G. J. Org. Chem. 1996, 61, 1875.
2. (b) Déziel, R.; Malenfant, E. J. Org. Chem. 1995, 61, 4660.
3. (c) Déziel, R.; Goulet, S.; Grenier, L.; Bordeleau, J.; Bernier, J. J. Org. Chem. 1993, 58, 3619.
4. For recent exemples of asymmetric reactions mediated with chiral organoselenium reagents: Fujita, K.; Murata, K.; Iwaoka, M.; Tomoda, S. Tetrahedron 1997, 53, 2029. Back, T. G.; Dyck, B. P. J. Chem. Soc., Chem. Commun. 1996, 2567. Wirth, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 1726. Nishibayashi, Y.; Srivastava, H.; Takada, S.; Fukuzawa, S.; Uemura, S. J. Chem. Soc., Chem. Commun. 1995, 2321.
5. For recent exemples of asymmetric reactions mediated with chiral organoselenium reagents: Fujita, K.; Murata, K.; Iwaoka, M.; Tomoda, S. Tetrahedron 1997, 53, 2029. Back, T. G.; Dyck, B. P. J. Chem. Soc., Chem. Commun. 1996, 2567. Wirth, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 1726. Nishibayashi, Y.; Srivastava, H.; Takada, S.; Fukuzawa, S.; Uemura, S. J. Chem. Soc., Chem. Commun. 1995, 2321.
6. For recent exemples of asymmetric reactions mediated with chiral organoselenium reagents: Fujita, K.; Murata, K.; Iwaoka, M.; Tomoda, S. Tetrahedron 1997, 53, 2029. Back, T. G.; Dyck, B. P. J. Chem. Soc., Chem. Commun. 1996, 2567. Wirth, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 1726. Nishibayashi, Y.; Srivastava, H.; Takada, S.; Fukuzawa, S.; Uemura, S. J. Chem. Soc., Chem. Commun. 1995, 2321.
7. For recent exemples of asymmetric reactions mediated with chiral organoselenium reagents: Fujita, K.; Murata, K.; Iwaoka, M.; Tomoda, S. Tetrahedron 1997, 53, 2029. Back, T. G.; Dyck, B. P. J. Chem. Soc., Chem. Commun. 1996, 2567. Wirth, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 1726. Nishibayashi, Y.; Srivastava, H.; Takada, S.; Fukuzawa, S.; Uemura, S. J. Chem. Soc., Chem. Commun. 1995, 2321.
8. Posner, G. H; Mallamo, J. P.; Black, A. Y. Tetrahedron 1981, 37, 3921.
9. DIP-Chloride is a trademark of Aldrich Chemical Co. Inc. For a recent review on this reagent see: Dhar, R. K. Aldrichim, Acta. 1994, 27, 43.
10. The enantiomeric purity of 7 was assessed by chiral HPLC analysis. The R, R diol was prepared from (+)-DIP-Cl.
11. Clive, D. L. J.; Chittattu, G. J.; Farina, V.; Keil, W. A.; Menchen, S. M.; Russell, C. G.; Singh, A.; Wong C. K.; Curtis, N. J. J. Am. Chem. Soc. 1980, 102, 4438.
12. Compain, P.; Goré, J.; Vatèle, J-M. Tetrahedron 1996, 52, 10405.