Acyclic stereoselection. 17. Simple diastereoselection in the addition of medium-and long-chain n-alkyl ketone lithium enolates to aldehydes
CH Heathcock, J Lampe
Index: Heathcock, , Clayton H.; Lampe, John Journal of Organic Chemistry, 1983 , vol. 48, # 23 p. 4330 - 4337
Full Text: HTML
Citation Number: 44
Abstract
The n-alkyl tert-butyl ketones lb-d have been prepared and the stereochemistry of their aldol reaction with benzaldehyde has been investigated. As with ketone la, ketones lb-d give 2 enolates that react with benzaldehyde in THF at-78" C to give syn aldols. When the aldol additions are carried out in pentane, the syn aldols are also the kinetic products, but syn-anti equilibration is much more rapid in this solvent; after reaction at 25" C for 20 min, ketones ...
Related Articles:
[Mello, Rossella; Martinez-Ferrer, Jaime; Alcalde-Aragones, Ana; Varea, Teresa; Acerete, Rafael; Gonzalez-Nunez, Maria Elena; Asensio, Gregorio Journal of Organic Chemistry, 2011 , vol. 76, # 24 p. 10129 - 10139]
[Conant; Webb; Mendum Journal of the American Chemical Society, 1929 , vol. 51, p. 1253]
[Conant; Webb; Mendum Journal of the American Chemical Society, 1929 , vol. 51, p. 1253]
[Conant; Webb; Mendum Journal of the American Chemical Society, 1929 , vol. 51, p. 1253]
[Whitmore et al. Journal of the American Chemical Society, 1941 , vol. 63, p. 647]