Stereoselective aldol condensations via boron enolates
DA Evans, JV Nelson, E Vogel…
Index: Evans,D.A.; Nelson,J.V.; Vogel,E. Journal of the American Chemical Society, 1981 , vol. 103, p. 3099
Full Text: HTML
Citation Number: 626
Abstract
Abstract: A detailed investigation of the enolization of a variety of ketones and carboxylic acid derivatives with dialkylboryl triflates in the presence of a tertiary amine and the subsequent aldol condensations of these boron enolates was conducted. The stereochemistry of the enolates formed from acyclic ketones was found to be dependent on the structure of the ketone, the dialkylboryl triflate, and the tertiary amine. A mechanism for ...
Related Articles:
Stereoselective synthesis of (S)-dapoxetine: a chiral auxiliary mediated approach
[Khatik, Gopal L.; Sharma, Ratnesh; Kumar, Varun; Chouhan, Mangilal; Nair, Vipin A. Tetrahedron Letters, 2013 , vol. 54, # 45 p. 5991 - 5993]
[Wang, Ying-Chuan; Yan, Tu-Hsin Journal of Organic Chemistry, 2000 , vol. 65, # 20 p. 6752 - 6755]
[Orsini, Fulvia; Sello, Guido; Manzo, Angelo Maria; Lucci, Elvira Maria Tetrahedron Asymmetry, 2005 , vol. 16, # 11 p. 1913 - 1918]
[Evans, D. A.; Bartroli, J.; Shih, T. L. Journal of the American Chemical Society, 1981 , vol. 103, # 8 p. 2127 - 2129]
[Boaz, Neil W. Journal of Organic Chemistry, 1992 , vol. 57, # 15 p. 4289 - 4292]