The Journal of Organic Chemistry

Acyclic stereoselection. 17. Simple diastereoselection in the addition of medium-and long-chain n-alkyl ketone lithium enolates to aldehydes

CH Heathcock, J Lampe

文献索引：Heathcock, , Clayton H.; Lampe, John Journal of Organic Chemistry, 1983 , vol. 48, # 23 p. 4330 - 4337

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被引用次数: 44

摘要

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 ...