Effects of Sterically Remote Substituents on 7r-Facial Stereoselectivity in Additions to Methylenecyclohexanes

Journal of the American Chemical Society

Volumn 109, Issue 19, 1987, Pages 5875-5876

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

^a WAYNE STATE UNIVERSITY   (United States)

^b FORDHAM UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845282043     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00253a064     Document Type: Article

References (17)

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12. nucleophilic additions to ketones, see: ref 1 and Danishefsky et al. (Danishefsky, S. J.; Langer, M. J. Org. Chem. 1985 50, 3672.).
13. Several earlier studied that pioneered this approach were flawed for various reasons: (a) Agami, C.; Kazakos, A.; Levisalles, J. Tetrahedron Lett. 1975, 16, 2035. (The C-3 substituents are axial.) Moreau, G. Bull. Soc. Chim. Fr. 1972, 2814. (The use of 2-;-Bu group to lock cyclohexanone conformation has been questioned, see: references in Cotterill, W. D.; Robinson, M. J. T. Tetrahedron 1964, 20, 765, 777.) Giddings, M. R.; Hudec, J. Can. J. Chem. 1981, 59, 459. (Wrong assignment of the diasteromer structures. see ref 1.)
14. (a) Klein, J. Tetrahedron Lett. 1973, 14, 4307. Klein, J. Tetrahedron 1974, 30, 3349.
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17. hexane derivatives, see ref 2. See, also: Brown, H. C.; Periasamy, M.; Perumal, P. T. J. Org. Chem. 1984, 49, 2754 (for a recent appraisal of the Baker-Nathan order problem). Edlund, U. Org. Magn. Reson. 1978, 11, 516 (for a demonstration of the Baker-Nathan order in the ground state).