A SIMPLE AND PRACTICAL SYNTHESIS OF 3,10-DISUBSTITUTED BETA-PINENE DERIVATIVES

The nopadiene - derived eta(3)-allyltitanium complex reacts with aldeh ydes regiospecifically at the ring carbon atom Two diastereomeric (Z) 10-methyl-beta-pinene-3-yl carbinols are isolated in a ratio depending on the aldehyde alkyl group. Other electrophiles can also be used ins tead of aldehydes. In this way, the ketone, ester, amide functions or hydrogen atom are introduced into the 3-position. Since other alpha-pi nene derived dienes can also be employed, the procedure should be rega rded as generally useful for the preparation of 3,10-bifunctionalized beta-pinene derivatives.