Asymmetric selenomethoxylation of alkenes with camphorselenenyl sulfate

Tetrahedron Letters

Volumn 39, Issue 18, 1998, Pages 2809-2812

  Tiecco, Marcello ^a   Testaferri, Lorenzo ^a   Santi, Claudio ^a   Marini, Francesca ^a   Bagnoli, Luana ^a   Temperini, Andrea ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AMMONIUM SULFATE; CAMPHOR; METHYL GROUP; REAGENT; SELENIDE; SELENIUM SULFATE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; METHYLATION; STEREOCHEMISTRY; THERMODYNAMICS;

DRYOBALANOPS;

EID: 0032580413     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00252-4     Document Type: Article

References (21)

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15. 6
16. 8. Similar changes in facial selectivity on passing from the bromide 2b to the sulfate 2d were also observed with styrene, α-methylstyrene and with the trans alkenes β-methylstyrene, 4-octene and methyl 3-hexenoate. No changes were observed with cyclohexene and cyclooctene. This effect of the counter anion on the facial selectivity of the addition reaction is presently under further investigation.
17. 9. Cram, D. J.; Kopecky, K. R.; Hauck, F.; Langemann, A. J. Am. Chem. Soc. 1959, 81, 5754-5760; Brown, H. C.; Chandrasekharan, J.; Ramachandran, P. V. J. Am. Chem. Soc. 1988, 110, 1539-1546.
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19. 1H-NMR in the presence of (S)-(+)-2,2,2-trifluoro-1-(9-anthryl)ethanol.
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21. 12. Further investigations on this selenenylation-elimination procedure, as well as on other asymmetric intermolecular and intramolecular addition reactions promoted by 2d, are presently under way.