Synthesis of β-Methyl Alcohols: Influence of Alkyl Chain Length on Diastereoselectivity and New Attractants of Rhynchophorus ferrugineus.

The diastereoselectivity of adducts in the addition reaction via the Felkin-Anh model is affected significantly by the steric effect of bulky groups. However, the influence of steric alkyl chain length has not been studied for the diastereoselectivity. In this work, we present a new strategy for the racemic synthesis of β-methyl alcohols to obtain various diastereomer ratios using the Felkin-Anh model. The addition of alkyl Grignard reagents to α-methyl aldehydes afforded diastereomer ratios of threo/erythro ≈ 2:1, while the reduction in structurally related ketones using LiAlH4 afforded ratios of threo/erythro ≈ 1:1. The experimental data showed no effect of alkyl chain length on either side on the stereoselectivity of adducts. All synthesized analogues were evaluated for attractiveness to Rhynchophorus ferrugineus weevils in the field. Five novel derivatives, including two alcohols and three ketones, were found to attract weevils in the field trials. Among them, 3-methyldecan-4-one (5b) and 4-methyldecan-5-ol (11a) were found to be the most attractive to the insects.