Iodocyclization of Allylic Alcohol Derivatives Containing Internal Nucleophiles. Control of Stereoselectivity by Substituents in the Acyclic Precursors

Journal of the American Chemical Society

Volumn 105, Issue 18, 1983, Pages 5819-5825

  Chamberlin, A Richard ^a   Dezube, Milana ^a   Dussault, Patrick ^a   McMills, Mark C ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS - REACTION KINETICS;

ALCOHOLS;

EID: 0021097053     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00356a020     Document Type: Article

References (18)

1. Bougault, M. J. C. R. Hebd. Seances Acad. Sci. 1904, 139, 864.
2. For reviews of halolactonization, see: (a) Dowle, M. D.; Davies, D.I. Chem. Soc. Rev. 1979, 171. (b) Staninets, V. I.; Shilov, E. A. Russ. Chem. Rev. {Engl. Transí.) 1971, 40, 272.
3. For recent examples of stereoselective halocyclization controlled by substituents in predominantly acyclic precursors, see: (a) Bartlett, P. A.; Myerson, J. J. Am. Chem. Soc. 1978, 100, 3950. (b) Terashima, S.; Hayashi, M.; Koga, K. Tetrahedron Lett. 1980, 21, 2733 and previous papers in the series, (c) Collum, D. B.; McDonald, J. H., III.; Still, W. C. J. Am. Chem. Soc. 1980, 102, 2118. (d) Takana, S.; Hirama, M.; Ogasawara, K. J. Org. Chem. 1980, 45, 3729. (e) Rychnovsky, S. D.; Bartlett, P. A. J. Am. Chem. Soc. 1981, 103, 3963. (f) Bartlett, P. A.; Myerson, J. J. Org. Chem. 1979, 44, 1625. (g) Corey, E. J.; Ease, T. Tetrahedron Lett. 1979, 32, 335.
4. Preliminary systematic study: Chamberlin, A. R.; Dezube, M.; Dussault, P. Tetrahedron Lett. 1981, 22, 4611. (b) First example (bromo-lactonization): Nakaminami, G.; Nakagawa, M.; Shioi, S.; Sugiyama, Y. Tetrahedron Lett. 1967, 3983. (c) Recent synthetic application: Rollinson, S. W.; Amos, R. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 4114.
5. Sharpless, K. B. Aldrichim. Acta 1979, 12, 63. In addition, the stereochemistry of the iodo lactones 3a and 3h have been determined by X-ray crystallographic analysis (see ref 4a and 9).
6. One of the few counterexamples to the general preference for γ- over δ-lactone formation (except in cases of overriding electronic factors or ring strain) is that 4-hexenoic acid reportedly gives the δ-lactone upon treatment with iodine: Staninets, V. I.; Shilov, E. A.; Koryak, E. B. Zh. Org. Khim. 1968, 4, 268.
7. Midland, M. M.; Holtermann, R.L. J. Org. Chem. 1981, 46, 1227 and references cited therein, (b) Bellucci, G.; Berti, G.; Bianchini, R.; Ing-rosso, G.; Mastrorilli, E. Gazz. Chim. Ital. 1976, 106, 955 and references cited therein.
8. An analogous regioselectivity has also been noted in reactions of epoxy alcohols: Buchanan, J. G.; Sable, H. Z. “Selective Organic Transformations, Thyagarajan, B. S., Ed.; Wiley: New York, 1972; Vol. 2, p. 1.
9. We use Heathcock's convention of threo/erythro nomenclature: Pirrung, M. C.; Heathcock, C.H. J. Org. Chem. 1980, 45, 1727. The starting threo acids 1j and 1k were prepared from their ethyl esters (no epimerization occurred during saponification), which in turn were available by the threo-selective methylation procedure reported by Frater and by Seebach: (a) Prater, G. Helv. Chim. Acta 1979, 62, 2825. (b) Seebach, D.; Wasmuth, D. Helv. Chim. Acta 1980, 63, 197. The corresponding erythro isomers were isolated from a mixture resulting from the condensation of lithio ethyl propionate with either acrolein or methacrolein.
10. Arnold, R. T.; Campos, M. M.; Lindsay, K.L. J. Am. Chem. Soc. 1953, 75, 1044 and references cited therein, (b) Jäger, V.; Günther, H. J. Tetrahedron Lett. 1977, 2543.
11. Gordon, A. J.; Ford, R. A. “The Chemists Companion” Wiley-Interscience: New York, 1972; p. 256 and references therein.
12. It has also been suggested that internal hydrogen bonding to the π-bond occurs (Nakaminami, G.; Shioi, S.; Sugiyama, Y.; Isemura, S.; Shi-buya, M.; Nakagawa, M. Bull. Chem. Soc. Jpn. 1972, 45, 2624). This idea is also ruled out.
13. Hall, H. K., Jr.; Brandt, M. K.; Mason, R.M. J. Am. Chem. Soc. 1958, 80, 6420.
14. Caramella, P.; Rondan, N. G.; Paddon-Row, M. N.; Houk, K.N. J. Am. Chem. Soc. 1981, 103, 2438.
15. For discussions of the concertedness of iodolactonization, see: (a) Williams, D. L. H.; Bienvenue-Goetz, E.; Dubois, J.E. J. Chem. Soc. B 1969, 517. (b) doAmaral, L.; Melo, S. C. J. Org. Chem. 1973, 38, 800. (c) Cambie, R. C.; Hayward, R. C.; Roberts, J. L.; Rutledge, P. S. J. Chem. Soc, Perkin Trans. 1 1974, 1864. (d) Reference 2b summarizes similar evidence for both iodolactonization and other, related processes.
16. Karabatsos, G. J.; Fenoglio, D. J. Top. Stereochem. 1970, 5, 167.
17. Kaiser, E. M.; Petty, J. D.; Knutson, P.L.A. Synthesis 1977, 509.
18. Sullivan, D. F.; Woodbury, M. W.; Rathke, M.W. J. Org. Chem. 1977, 42, 2038.