| Title: | Synthesis of beta-Methyl Alcohols: Influence of Alkyl Chain Length on Diastereoselectivity and New Attractants of Rhynchophorus ferrugineus |
| Author(s): | Le VD; Dang CH; Nguyen CH; Nguyen HU; Nguyen TD; |
| Address: | "Graduate University of Science and Technology, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Cau Giay, Hanoi 100000, Vietnam. Institute of Chemical Technology, Vietnam Academy of Science and Technology, 1A, TL29, District 12, Ho Chi Minh City 70000, Vietnam. Department of Agriculture and Aquaculture, Tra Vinh University, 126 Nguyen Thien Thanh Street Ward 5, Tra Vinh City 87000, Vietnam" |
| ISSN/ISBN: | 1520-5118 (Electronic) 0021-8561 (Linking) |
| Abstract: | "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 beta-methyl alcohols to obtain various diastereomer ratios using the Felkin-Anh model. The addition of alkyl Grignard reagents to alpha-methyl aldehydes afforded diastereomer ratios of threo/erythro approximately 2:1, while the reduction in structurally related ketones using LiAlH(4) afforded ratios of threo/erythro approximately 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" |
| Keywords: | Alcohols Animals Ketones Methanol *Weevils Felkin-Anh model Grignard coupling diastereoselectivity microwave irradiation pheromone; |
| Notes: | "MedlineLe, Van-Dung Dang, Chi-Hien Nguyen, Cong-Hao Nguyen, Hong-Ung Nguyen, Thanh-Danh eng 2021/05/25 J Agric Food Chem. 2021 Jun 2; 69(21):5882-5886. doi: 10.1021/acs.jafc.1c01875. Epub 2021 May 24" |
