Tetrahedron p. 523 - 544 (1990)
Update date:2022-09-26
Topics:
Cain, Christian M.
Cousins, Richard P. C.
Coumbarides, Greg
Simpkins, Nigel S.
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.
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