65970-71-0Relevant academic research and scientific papers
Oxidation of homochiral ketals by rhenium(VII) oxide. V
Tang,Kennedy
, p. 7823 - 7826 (2007/10/02)
2-Hydroxyethyl enol ethers react with Re2O7 to produce 2-hydroxyketals. Where homochiral starting enol ethers are employed, greater than 99:1 diastereoselectivities are obtained. The stereocontrol is rationalized by invoking a transition state that approximates the geometry of a metallaoxetane. Finally, homochiral ketals are themselves oxidized to provide 2-hydroxyketals with high diastereoselectivity.
ASYMMETRIC DEPROTONATION OF PROCHIRAL KETONES USING CHIRAL LITHIUM AMIDE BASES
Cain, Christian M.,Cousins, Richard P. C.,Coumbarides, Greg,Simpkins, Nigel S.
, p. 523 - 544 (2007/10/02)
A number of chiral secondary amines have been prepared and used as precursors to the corresponding chiral lithium amide bases.Treatment of either cis-2,6-dimethylcyclohexanone or 4-tert-butylcyclohexanone with a chiral lithium amide, followed by electrophilic quench, gives chiral products in up to 88 percent enantiomeric excess.The results with 4-tert-butylcyclohexanone are in disagreement with an earlier literature report, giving products of lower enantiomeric excess but higher optical rotation.
Chiral products via asymmetric deprotonation of 4-tert-butylcyclohexanone using chiral lithium amide bases
Cousins,Simpkins
, p. 7241 - 7244 (2007/10/02)
The asymmetric deprotonation of 4-tert-butylcyclohexanone using chiral lithium amide bases gives derived silyl enol ether products in up to 88% ee.
ASYMMETRIZATION OF MESO-CYCLIC KETONES USING HOMOCHIRAL ACETAL TEMPLATES
Naruse, Yuji,Yamamoto, Hisashi
, p. 6021 - 6030 (2007/10/02)
Employing the homochiral acetal template, asymmetrization of meso-substituted cyclohexanones is explored.By the use of optically-active 2,4-pentanediol as a chiral protecting group, highly diastereoselective acetal cleavage is achieved when treated with organoaluminum reagent.Dialkylaluminum amides are also effective reagents for this reaction.
