Asymmetric Selenomethoxylation of Olefins Involving a Chiral C2 Symmetrical Electrophilic Organoselenium Reagent

Journal of Organic Chemistry

Volumn 58, Issue 14, 1993, Pages 3619-3621

  Déziel, Robert ^a   Goulet, Sylvie ^a   Grenier, Louis ^a   Bordeleau, Josée ^a   Bernier, Julie ^a  

^a BOEHRINGER INGELHEIM CANADA LTD   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000102337     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00066a010     Document Type: Article

References (21)

1. For excellent reviews on organoselenium chemistry, see: (a) Organoselenium Chemistry; Liotta, D., Ed.; Wiley: London, 1987.
2. Selenium Reagents and Intermediates in Organic Synthesis; Paulmier, C., Ed.; Pergamon Press: Oxford, 1986.
3. Schmid, G. H.; Garratt, D. G. In The Chemistry of Double-Bonded Functional Groups; Patai, S., Ed., Wiley: London, 1977; Supp. A, Part 2.
4. Garratt, D. G.; Kabo, A. Can. J. Chem. 1980, 58, 1030.
5. Binaphthyl-based chiral organoselenium derivatives have already been reported but low asymmetric induction was observed from these compounds. (a) Tomoda, S.; Iwaoka, M. Chem. Lett. 1988, 1895.
6. Tomoda, S.; Fujita, K.; Iwaoka, M. J. Chem. Soc., Chem. Commun. 1990, 129.
7. 2 symmetry see: Whitesell, J. K. Chem. Rev. 1989, 89, 1581.
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14. Prepared according to: Mathre, D. J.; Jones, T. K.; Xavier, L. C.; Blacklock, T. J.; Reamer, R. A.; Mohan, J. J.; Turner Jones, E. T.; Hoogstean, K.; Baum, M. W.; Grabowski, E. J. J. J. Org. Chem. 1991, 56, 751.
15. For leading references on the regiochemistry of addition of phenylselenyl halides to olefins, see (a) Liotta, D.; Zima, G. Tetrahedron Lett. 1978, 4977.
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