Diastereoselective Route to Enantiomerically Pure Homoallylic Pinene Alcohols from Myrtenyl Bromide and Aldehydes

Article abstract of DOI:10.1016/S0957-4166(00)80458-9

With zinc dust in aq.NH4Cl/THF, myrtenyl bromide (1) reacts with aldehydes (2) to give simple new pinene alcohols (β-pinene-3-yl carbinols) (3), which are enantiomerically pure (100percent de).The configuration of the new chiral centre at C-11 was determined by oxidation to the ketone 4 and stereoselective reduction to Cram alcohol 3.