1838-73-9Relevant 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.
Electrochemical alkyl transfer reactions of trialkylborane to carbonyl compounds by use of copper sacrificial anode
Choi, Jung Hoon,Youm, Jong Sung,Cho, Cheon-Gyu,Czae, Myung-Zoon,Hwang, Book Kee,Kim, Jung Sung
, p. 4835 - 4838 (2007/10/03)
Alkyl groups in trialkylboranes were successfully transferred to carbonyl compounds in the presence of the platinum cathode and copper anode by electrochemical method. The new, mild electrochemical alkyl transfer reaction produced various substituted alcohols in good yields.
-WITTIG SIGMATROPIC REARRANGEMENT OF CROTYL PROPARGYL ETHER SYSTEM; AN EMERGING TOOL FOR CONTROL OF ACYCLIC STEREOCHEMISTRY
Mikami, Koichi,Azuma, Ken-Ichi,Nakai, Takeshi
, p. 2303 - 2308 (2007/10/02)
The -Wittig rearrangement of properly designated (E)- and (Z)-crotyl propargyl ether system has been shown to exhibit a remarkably high degree of threo- and erythro-selection, respectively, and the stereochemical outcomes are discussed on mechanistic grounds.Some useful transformations of the rearrangement product are also described within the context of the formal total synthesis of (+/-)-oudemansin.Further, the high level of diastereoselection is maintained in the reaction of the α-methylcrotyl counterparts, together with the exclusive formation of the (E)-olefinic bond.
Stereochemistry of Aliphatic Carbocations, 13. Protonated Cyclopropanes as Intermediates in 1,2-Alkyl Shifts
Kirmse, Wolfgang,Loosen, Karin,Prolingheuer, Ernst-Christoph
, p. 129 - 141 (2007/10/02)
The nitrous acid deamination of 2-ethyl-1-methylbutylamine (10), 1,2-diethylbutylamine (35), and 2-ethyl-1-methylpentylamine (43) has been studied with respect to 1,2-alkyl shifts.Optically active and deuterated amines were employed whenever possible.The structure, configuration, and deuterium distribution of various products (e. g. 16 from 10, 40 and 48 from 35, 56 from 43) are most reasonably explained in terms of alkyl-bridged intermediates (corner-protonated cyclopropanes) which isomerize via proton shifts from corner to corner.The alternative interconversion of open ions via 1,3-H shifts is incompatible with our experimental results.
