Intramolecular bicyclization of hydroxypentynyliodonium triflate derivatives to furnish cyclopentannelated tetrahydrofurans: The first examples of cyclopentene formation following alkoxide addition to alkynyliodonium salts

Tetrahedron Letters

Volumn 39, Issue 19, 1998, Pages 2911-2914

  Feldman, Ken S ^a   Bruendl, Michelle M ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTENE DERIVATIVE; DIPHENYLIODONIUM SALT; TETRAHYDROFURAN;

ARTICLE; CYCLIZATION; DERIVATIZATION; DRUG SYNTHESIS; ENZYME SUBSTRATE; MOLECULAR INTERACTION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0032492967     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00415-8     Document Type: Article

References (17)

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3. c) Koser, G. F., in "Supplement D2: The Chemistry of Halides, Pseudo-halides and Azides", Patai, S. and Rappoport, Z., Eds. John Wiley and Sons Ltd (1995), p 1173.
4. 2. a) Stang, P. J. Acc. Chem. Res. 1991, 24, 304.
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6. c) Kitamura, T.; Zheng, L.; Taniguchi, H.; Sakurai, M.; Tanaka, R. Tetrahedron Lett. 1993, 34, 4055.
7. d) Kitamura, T.; Zheng, L.; Fukuoka, T.; Fujiwara, Y.; Taniguchi, H.; Sakurai, M.; Tanaka, R. J. Chem Soc., Perkin Trans. 2 1997, 1511.
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9. f) Ochiai, M.; Kumshima, M.; Fuji, K.; Nagao, Y. J. Org. Chem. 1988, 53, 6144.
10. 3. a) Feldman, K. S.; Bruendl, M. M.; Schildknegt, K.; Bohnstedt, A. C. J. Org. Chem. 1996, 61, 5440.
11. b) Feldman, K. S.; Bruendl, M. M.; Schildknegt, K. J. Org. Chem. 1995, 60, 7722.
12. c) Schildknegt, K.; Bohnstedt, A. C.; Feldman, K. S; Sambandam, A. J. Am. Chem. Soc. 1995, 117, 7544. For example, (equation presented)
13. 2: C, 81.60; H, 7.53; Found: C, 81.58; H, 7.47. (equation presented)
14. 5. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
15. 6. a) See ref. 1a, p 1154.
16. b) For examples of 2-lithiofuran displacing an alkyne anion from alkynyl(aryl)iodonium tosylates, see Margida, A. J.; Koser, G. F. J. Org. Chem. 1984, 49, 4703.
17. + species are reduced to alcohol with concomitant oxidation of solvent. Thus, treament of alkoxide i with alkynyliodonium salt 2 in THF gave no intermolecular addition products, but did provide a 33 % yield of the known THF adduct iii, Presumably, oxidation of THF to the electrophilic carbenium ion ii is followed by trapping with i. (equation presented)