Abstract
The ene-type chlorination of terpene alcohols (1) such as linalool and geraniol with hypochlorous acid gave allylic chlorides (2) in good yields. Allylic chlorides (2) reacted with Grignard reagents such as isopentylmagnesium bromide and 3, 7-dimethyloctylmagnesium bromide in the presence of CuCl to give γ-cross coupling products (5) and (6) such as 6, 7-dehydroisophytol (5 b, 6 b) and 6, 7-dehydrophytol (5 d, 6 d) with high regioselectivities.
