Stereochemical features of iodocyclisations of 3-alkene-1,2-diols to β- hydroxytetrahydrofurans

Tetrahedron Letters

Volumn 41, Issue 22, 2000, Pages 4447-4451

  Bew, Sean P ^a   Barks, Jenny M ^b   Knight, David W ^a   Middleton, Robert J ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

3 alkene 1,2 diols; 5 endo; Iodocyclisation; Stereoselective; Tetrahydrofurans

Indexed keywords

ALKANEDIOL DERIVATIVE; TETRAHYDROFURAN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; IODINATION; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

EID: 0034622024     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00613-4     Document Type: Article

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18. Cf., Rychnovsky, S. D.; Bartlett, P. A. J. Am. Chem. Soc. 1981, 103, 3963; Bartlett, P. A.; Holmes, C. P. Tetrahedron Lett. 1983, 24, 1365; Marek, I.; Lefrançois, J.-M.; Normant, J.-F. Tetrahedron Lett. 1992, 33, 1747; Walkup, R. D.; Guan, L.; Kim, S. W.; Kim, Y. S. Tetrahedron Lett. 1992, 33, 3969; Dehmlow, H.; Mulzer, J.; Seilz, C.; Strecker, A. R.; Kohlmann, A. Tetrahedron Lett. 1992, 33, 3607.
19. Cf., Rychnovsky, S. D.; Bartlett, P. A. J. Am. Chem. Soc. 1981, 103, 3963; Bartlett, P. A.; Holmes, C. P. Tetrahedron Lett. 1983, 24, 1365; Marek, I.; Lefrançois, J.-M.; Normant, J.-F. Tetrahedron Lett. 1992, 33, 1747; Walkup, R. D.; Guan, L.; Kim, S. W.; Kim, Y. S. Tetrahedron Lett. 1992, 33, 3969; Dehmlow, H.; Mulzer, J.; Seilz, C.; Strecker, A. R.; Kohlmann, A. Tetrahedron Lett. 1992, 33, 3607.
20. Cf., Rychnovsky, S. D.; Bartlett, P. A. J. Am. Chem. Soc. 1981, 103, 3963; Bartlett, P. A.; Holmes, C. P. Tetrahedron Lett. 1983, 24, 1365; Marek, I.; Lefrançois, J.-M.; Normant, J.-F. Tetrahedron Lett. 1992, 33, 1747; Walkup, R. D.; Guan, L.; Kim, S. W.; Kim, Y. S. Tetrahedron Lett. 1992, 33, 3969; Dehmlow, H.; Mulzer, J.; Seilz, C.; Strecker, A. R.; Kohlmann, A. Tetrahedron Lett. 1992, 33, 3607.
21. Cf., Rychnovsky, S. D.; Bartlett, P. A. J. Am. Chem. Soc. 1981, 103, 3963; Bartlett, P. A.; Holmes, C. P. Tetrahedron Lett. 1983, 24, 1365; Marek, I.; Lefrançois, J.-M.; Normant, J.-F. Tetrahedron Lett. 1992, 33, 1747; Walkup, R. D.; Guan, L.; Kim, S. W.; Kim, Y. S. Tetrahedron Lett. 1992, 33, 3969; Dehmlow, H.; Mulzer, J.; Seilz, C.; Strecker, A. R.; Kohlmann, A. Tetrahedron Lett. 1992, 33, 3607.
22. Cf., Rychnovsky, S. D.; Bartlett, P. A. J. Am. Chem. Soc. 1981, 103, 3963; Bartlett, P. A.; Holmes, C. P. Tetrahedron Lett. 1983, 24, 1365; Marek, I.; Lefrançois, J.-M.; Normant, J.-F. Tetrahedron Lett. 1992, 33, 1747; Walkup, R. D.; Guan, L.; Kim, S. W.; Kim, Y. S. Tetrahedron Lett. 1992, 33, 3969; Dehmlow, H.; Mulzer, J.; Seilz, C.; Strecker, A. R.; Kohlmann, A. Tetrahedron Lett. 1992, 33, 3607.
23. For stereoselective approaches, see: Mead, K. T. Tetrahedron Lett. 1987, 28, 1019 (syn selective); Alami, M.; Crousse, B.; Linstrumelle, G.; Mambu, L.; Larchevêque, M. Synlett 1993, 217 (anti selective).
24. For stereoselective approaches, see: Mead, K. T. Tetrahedron Lett. 1987, 28, 1019 (syn selective); Alami, M.; Crousse, B.; Linstrumelle, G.; Mambu, L.; Larchevêque, M. Synlett 1993, 217 (anti selective).
25. Jeong, K.-S.; Sjö, P.; Sharpless, K. B. Tetrahedron Lett. 1992, 33, 3833. In the AD version, only (E)-enynes give high enantioselectivities; (Z)-enynes give variable ees (30-70%). Thus, at least (E)-enynes could be used as precursors to enantiopure hydroxytetrahydrofurans of the types described herein.
26. Full analytical and spectroscopic data have been obtained for all compounds reported, with the exception of some of the minor products 11, 14, 17 and 20.
27. For an application, see the following paper: Bew, S. P.; Knight, D. W.; Middleton, R. J. Tetrahedron Lett. 2000, 41, 000-000.