Nucleophile-Selective Iodocyclizations: Butyrolactone versus Tetrahydrofuran Formation

Journal of the American Chemical Society

Volumn 111, Issue 10, 1989, Pages 3712-3717

  Kurth, Mark J ^a   Beard, Richard L ^a   Olmstead, Marilyn ^a   Macmillan, James G ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF NORTHERN IOWA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000183056     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00192a032     Document Type: Article

References (11)

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2. Bongini, A.; Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. J. Org. Chem. 1986, 51, 4905. Bartlett, P. A.; Ting, P. C. J. Org. Chem. 1986, 51, 2230. Beak, P.; Wilson, D. J. Org. Chem. 1987, 52, 218. Bergman, N.-Á.; Jausson, M. J. Org. Chem. 1987, 52, 4449.
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4. Kurth, M. J.; Brown, E. G. J. Am. Chem. Soc. 1987, 109, 6844.
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6. Bordwell, F.; Hughes, D. L. J. Am. Chem. Soc. 1984, 106, 3234.
7. 9b while that of a carboxylic acid is about 4.7. On the basis of Bordwell consideration, the carboxylate is expected to be a much better nucleophile than the ester, Arnett, E. M. Prog. Phys. Org. Chem. 1963, 1, 324.
8. 10b was thwarted by elimination to the α,β-unsaturated ester, Swain, M. L.; Turner, R. W. J. Chem. Soc., Chem. Commun. 1981, 840.
9. See ref 2c. Seebach, D.; Thaisrivongs, S. J. Am. Chem. Soc. 1983, 105, 7407. Kozikowski, A. P.; Stein, P. D. J. Org. Chem. 1984, 49, 2301.
10. For a discussion of reactivity as a function of time and proximity, see: Menger, F. M. Acc. Chem. Res. 1985, 18, 128.
11. Houk, K. N.; Paddon-Row, N.; Rondan, N. G.; Wu, Y.-D.; Brown, F. K.; Spellmeyer, D. C.; Metz, J. T.; Li, Y.; Loncharich, R. J. Science 1986, 231, 1108-17.