Synthetic Route of C15H16O2In 2002, Ohmori, Ken;Hachisu, Yoshifumi;Suzuki, Takao;Suzuki, Keisuke published 《Stereogenic tert-alcohols via group-selective hydroalumination: further scope》. 《Tetrahedron Letters》published the findings. The article contains the following contents:
Two classes of bis-alkynyl alcs. were subjected to hydroalumination reaction, which, under suitable conditions, proceeded in a highly group-selective manner. The first set of reactants comprised (4R,5S)-5-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-α,α-di-1-hexynyl-2,2-dimethyl-1,3-dioxolane-4-methanol (I) and (4R,5S)-α,α-di-1-hexynyl-5-[(methoxyethoxy)methyl]-2,2-dimethyl-1,3-dioxolane-4-methanol. The second set of reactants comprised (4S)-α,α-di-1-hexynyl-2,2-dimethyl-1,3-dioxane-4-methanol (II) and (4S)-α,α-di-1-hexynyl-2,2-diphenyl-1,3-dioxane-4-methanol. The reaction of I with butyllithium/DIBAL gave (-)-5-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-α-1-hexenyl-α-1-hexynyl-2,2-dimethyl-1,3-dioxolane-4-methanol as the major product stereoselectively. Hydroalumination of II gave a 73/27 mixture of (4S)-α-1-hexenyl-α-1-hexynyl-2,2-dimethyl-1,3-dioxane-4-methanol (III) and its epimer. Group selectivity was changed using ethylmagnesium bromide as the reagent, thus yielding the epimer of III as the major product. And Dimethoxydiphenylmethane (cas: 2235-01-0) was used in the research process.
The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom.Synthetic Route of C15H16O2
Reference:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem