Experimental tests of models to predict nucleophilic addition stereochemistries

D Mukherjee, YD Wu, FR Fronczek…

Index: Mukherjee, Debabrata; Wu, Yun-Dong; Fronczek, Frank R.; Houk, K. N. Journal of the American Chemical Society, 1988 , vol. 110, # 10 p. 3328 - 3330

Full Text: HTML

Citation Number: 53

Abstract

5 operates in unhindered cases, so that axial attack of the nucleophile produces the more stable equatorial alcohol in each case. 6 Felkin suggested that the preference for axial attack on unhindered cyclohexanones is due to the greater torsional strain which occurs in the transition state of equatorial atta~ k,~ as shown in 2. Attack at any chosen trajectory on the carbonyl group of 2 is more eclipsed from the equatorial direction. This conformation is ...