Reversal of π-Facial Diastereoselection Upon Electronegative Substitution of the Substrate and the Reagent

Journal of the American Chemical Society

Volumn 111, Issue 22, 1989, Pages 8447-8462

  Cieplak, Andrzej S ^a   Tait, Bradley D ^b   Johnson, Carl R ^b  

^a FORDHAM UNIVERSITY   (United States)

^b WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845183424     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00204a018     Document Type: Article

References (113)

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101. Froimowitz, M.; Cieplak, A. S., unpublished.
102. 86a,88
103. 3 methyl groups in 2,2,6,6-tetramethylpiperidine produces therefore a significant ring distortion (examination of the Cambridge Structural Database 1986 Version I reveals that the tetrahedral valency angle on the nitrogen found in piperidines is increased to the trigonal value in 2,2,6,6-tetramethylpiperidines, 122°, SD 4.6°, 62 entries). Since ionization potentials of amines and ethers are known to decrease when the ring size and the endocyclic valency angle increase (Yoshikawa, K.; Hashimoto, M.; Morishima, I. J. Am. Chem. Soc. 1974, 96, 288. Levy, G.; De Loth, P. C. R. Acad. Sci. Ser. C 1974, 279C, 331), this distortion seems to be the most likely reason for the extra decrease in the 2,2,6,6-tetramethylpiperidine case.
104. 41cemphasized Lewis acid promotion of the more hindered approach in these reactions; see also: Quintard, J.-P.; Pereyre, M. Bull. Soc. Chim. Fr. 1972, 1950. For the most dramatic examples of the Lewis acid effect, see: Marouka, K.; Itoh, T.; Sakurai, M.; Nonoshita, K.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 3588. Ashby, E. C.; Yu, S.; Roling, P. V. J. Org. Chem. 1972, 37, 1918. Laemmle, J. T.; Ashby, E. C.; Roling, P. V. J. Org. Chem. 1973, 38, 2526. For a recent review of enantioselective carbonyl additions that involve Lewis acid incorporation into the transition state, see: Evans, D. A. Science 1988, 240, 420.
105. Gassman, P. G.; Schaffhausen, J. G.; Reynolds, P. W. J. Am. Chem. Soc. 1982, 104, 6408. Gassman, P. G,; Schaffhausen, J. G.; Starkey, F. D.; Raynolds, P. W. J. Am. Chem. Soc. 1982, 104, 6411. Hoffman, R. W.; Hauel, N. Landman, B. Chem. Ber. 1983, 116, 389. Paquette, L. A.; Klinger, F.; Hertel, L. W. J. Org. Chem. 1981, 46, 4403. Paquette, L. A.; Hertel, L. W.; Gleiter, R.; Bohm, M. C.; Beno, M. A.; Christoph, G. G. J. Am. Chem. Soc. 1981, 103, 7106. Okada, K.; Tomita, S.; Oda, M. Tetrahedron Lett. 1986, 27, 2645.
106. cs, see: Bernardi, F.; Bottoni, A.; Fossey, J.; Sorba, J. Tetrahedron 1986, 42, 5567. It is interesting to note that under these assumptions, the Cieplak model provides a simple rationalization of the increasing number of data on stereochemistry of cycloadditions to 5-substituted cyclopentadienes: Woodward, R. B.; Katz, T. J. Tetrahedron 1969, 5, 70. Winstein, S.; Shatavsky, M.; Norton, C.; Woodward, R. B. J. Am. Chem. Soc. 1955, 77, 4183. Jones, D. W. J. Chem. Soc., Chem. commun. 1980, 739. Macaulay, J. B.; Fallis, A. J. Am. Chem. Soc. 1988, 110, 4074. Breslow, R.; Hoffman, J. M. H., Jr.; Perchonock, C. Tetrahedron Lett. 1973, 3723. As expected, electronegative substitution of the reagent reverses the preference for the less hindered approach in favor of the more hindered approach that is anti to the better a donor: Williamson, K. L.; Hsu, L. Y.; Lacko, R.; Youn, C. H. J. Am. Chem. Soc. 1969, 91, 6129. Williamson, K. L.; Li Hsu, Y. F. J. Am. Chem. Soc. 1970, 92, 7385. The latter phenomenon was also observed in the case of cycloadditions of nitrile oxides to 3,4-dichlorocyclobutene (Bianchi, G.; De Micheli, C.; Gamba, A.; Gandolfi, R. J. Chem. Soc., Perkin Trans. 1 1974, 137, compare entries d-and g-j in Table I, p 138) but the replacement of Cl by S does not reverse the syn preference observed in cycloadditions of diazomethanes in this system and the reason for the discrepancy is not apparent: Landen, H.; Margraf, B.; Martin, H.-D.; Steigel, A. Tetrahedron Lett. 1988, 29, 6597. For another example of the anti approach to a better σ donor in cycloaddition reactions, see: Dolbier, W. R., Jr.; Wicks, G. E.; Burkholder, C. R. J. Org. Chem. 1987, 52, 2196. Dolbier, W. R., Jr.; Burkholder, C. R.; Wicks, G. E.; Palenik, G. J.; Gawron, M. J. Am. Chem. Soc. 1985, 107, 7183.
107. 80a
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110. To the best of our knowledge, this conclusion was formulated for the first time in 1962: Kamernitskii, A. V.; Akhrem, A. A. Tetrahedron 1962, 18, 705.
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