Nucleophilic Additions to 4,4-Disubstituted 2,5-Cyclohexadienones: Can Dipole Effects Control Facial Selectivity?

Chemical Reviews

Volumn 99, Issue 5, 1999, Pages 1469-1480

  Wipf, Peter ^a   Jung, Jae Kyu ^a,b  

^a UNIVERSITY OF PITTSBURGH   (United States)

^b Hanwha Corporation   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000428270     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr9803838     Document Type: Article

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124. The conformer with the larger dipole moment is often, but not always, the less stable one. See, for example: Perrin, C. L.; Young, D. B. Tetrahedron Lett. 1995, 36, 7185. The minimization of dipole moments in the transition state can also play an important role in determining the observed diastereoselectivity: Jones, D. K.; Liotta, D. C.; Choi, W.-B.; Volante, R. P.; Reider, P. J.; Shinkai, I.; Churchill, H. R. O.; Lynch, J. E. J. Org. Chem. 1994, 59, 3749.