20754-04-5Relevant academic research and scientific papers
Synthesis of β-Methyl Alcohols: Influence of Alkyl Chain Length on Diastereoselectivity and New Attractants of Rhynchophorus ferrugineus
Le, Van-Dung,Dang, Chi-Hien,Nguyen, Cong-Hao,Nguyen, Hong-Ung,Nguyen, Thanh-Danh
, p. 5882 - 5886 (2021/06/21)
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.
Addition of organocerium reagents to morpholine amides: synthesis of important pheromone components of Achaea janata.
Badioli, Michele,Ballini, Roberto,Bartolacci, Massimo,Bosica, Giovanna,Torregiani, Elisabetta,Marcantoni, Enrico
, p. 8938 - 8942 (2007/10/03)
Readily preparable morpholine amides hitch in good yields with organocerium reagents to produce ketones. Even in the presence of substrates and reagents with high steric hindrance, the organometallic compounds prepared from dry cerium(III) chloride and organomagnesium or organolithium compounds at -78 degrees C add cleanly to morpholine amides. The low cost of starting materials makes this new scheme of synthesis very interesting for the preparation of biologically important pheromones.
Salt effects on the reactivity and the stability of organomanganese reagents
Cahiez, Gerard,Razafintsalama, Lynah,Laboue, Blandine,Chau, Francois
, p. 849 - 852 (2007/10/03)
The reactivity and the stability of organomanganese reagents prepared from the ate complexes MnX2·2LiBr (X= Br,I) and MnCl2·R4NX (X= Br, Cl) were studied. The preparation and the use for synthetic applications of stable sec- and tert-alkylmanganese bromides in ether as well as the acylation of RMnCl by R'COOCOOEt in THF were successfully achieved for the first time.
