Journal of Organic Chemistry p. 3831 - 3836 (1989)
Update date:2022-08-04
Topics:
Taber, Douglass F.
Mack, James F.
Rheingold, Arnold L.
Geib, Steven J.
The α-formyl ester derived from 2-(1-naphthyl)-3-borneol, as the potassium salt in moist dimethoxymethane, adds to methyl vinyl ketone to give two adducts in a ratio of 95:5.The relative configuration of the major diastereomer has been confirmed by X-ray crystallography.This diastereomer is readily carried on to (+)-O-methyljoubertiamine.The addition of such naphthylbornyl esters to Michael acceptors should constitute a general laboratory-scale procedure for the enantioselective construction of enantiomerically pure quaternary stereogenic centers.
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