Unusual reactivity of sulfahydantoins in the Mitsunobu reaction

Tetrahedron Letters

Volumn 39, Issue 41, 1998, Pages 7435-7438

  Dewynter, Georges ^a   Ubaldi, Sophie ^b   Voyer, Normand ^b   Toupet, Loic ^c  

^a UNIV MONTPELLIER   (France)

^b UNIVERSITÉ LAVAL   (Canada)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

HYDANTOIN DERIVATIVE; SULFAHYDANTOIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

EID: 0032497611     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01630-X     Document Type: Article

References (21)

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9. -3, D/s 0.25, 0.29 Max 2Θ (°) 50°
10. 8-Only one diastereoisomer was detected in the crude reaction mixture by NMR ruling out the possibility of a selective enrichment during crystallization.
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12. 9-Oppolzer, W.; Chapuis, C.; Bernadinelli, G. Helv. Chim. Acta 1984, 67, 1397. Bernadinelli, G.; Oppolzer, W.; Dupuis, CD. Acta Crystall., sect. C 1986, 42, 1460. Bernadinelli, G.; Oppolzer, W.; Schneider, P. Acta Crystall., sect. C 1987, 43, 1000. Oppolzer, W.; Poli, G.; Starkemann, C.; Bernadinelli, G. Tetrahedron Lett. 1988, 29, 3559.
13. 9-Oppolzer, W.; Chapuis, C.; Bernadinelli, G. Helv. Chim. Acta 1984, 67, 1397. Bernadinelli, G.; Oppolzer, W.; Dupuis, CD. Acta Crystall., sect. C 1986, 42, 1460. Bernadinelli, G.; Oppolzer, W.; Schneider, P. Acta Crystall., sect. C 1987, 43, 1000. Oppolzer, W.; Poli, G.; Starkemann, C.; Bernadinelli, G. Tetrahedron Lett. 1988, 29, 3559.
14. 9-Oppolzer, W.; Chapuis, C.; Bernadinelli, G. Helv. Chim. Acta 1984, 67, 1397. Bernadinelli, G.; Oppolzer, W.; Dupuis, CD. Acta Crystall., sect. C 1986, 42, 1460. Bernadinelli, G.; Oppolzer, W.; Schneider, P. Acta Crystall., sect. C 1987, 43, 1000. Oppolzer, W.; Poli, G.; Starkemann, C.; Bernadinelli, G. Tetrahedron Lett. 1988, 29, 3559.
15. 10-Castro, J.L.; Matassa, V.G. J. Org. Chem. 1994, 59, 2289. Other zwitterionic CSI-derived structures were also reported in: Kang, J.S.; Oh, D.Y. Heterocycles 1986, 24, 2255. Friedrichsen, W.; Bottcher, A.; Debaer-demaeker, T.Heterocycles 1983, 20, 845. Burgess, E.M.; Penton, H.R.Jr.; Taylor, E.A.; Williams, W.M. Org. Synth. 1988, VI, 788.
16. 10-Castro, J.L.; Matassa, V.G. J. Org. Chem. 1994, 59, 2289. Other zwitterionic CSI-derived structures were also reported in: Kang, J.S.; Oh, D.Y. Heterocycles 1986, 24, 2255. Friedrichsen, W.; Bottcher, A.; Debaer-demaeker, T.Heterocycles 1983, 20, 845. Burgess, E.M.; Penton, H.R.Jr.; Taylor, E.A.; Williams, W.M. Org. Synth. 1988, VI, 788.
17. 10-Castro, J.L.; Matassa, V.G. J. Org. Chem. 1994, 59, 2289. Other zwitterionic CSI-derived structures were also reported in: Kang, J.S.; Oh, D.Y. Heterocycles 1986, 24, 2255. Friedrichsen, W.; Bottcher, A.; Debaer-demaeker, T.Heterocycles 1983, 20, 845. Burgess, E.M.; Penton, H.R.Jr.; Taylor, E.A.; Williams, W.M. Org. Synth. 1988, VI, 788.
18. 10-Castro, J.L.; Matassa, V.G. J. Org. Chem. 1994, 59, 2289. Other zwitterionic CSI-derived structures were also reported in: Kang, J.S.; Oh, D.Y. Heterocycles 1986, 24, 2255. Friedrichsen, W.; Bottcher, A.; Debaer-demaeker, T.Heterocycles 1983, 20, 845. Burgess, E.M.; Penton, H.R.Jr.; Taylor, E.A.; Williams, W.M. Org. Synth. 1988, VI, 788.
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20. 12-Another possible mechanism would be the phosphorylation of the lactim form of 1 followed by an addition-elimination process by the alcohol.
21. 13-We have synthesized by a different strategy the following N-benzyl compound and showed that it does not interconvert to the O-alkylated analog. (equation presented)