ASYMMETRIC DEPROTONATION OF PROCHIRAL KETONES USING CHIRAL LITHIUM AMIDE BASES
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.
Cain, Christian M.,Cousins, Richard P. C.,Coumbarides, Greg,Simpkins, Nigel S.
p. 523 - 544
(2007/10/02)
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