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- W2939336497 abstract "Enantioselective allylboration of aldehydes with α-substituted β-methyl allylboronate was reported. By using BF3·OEt2 as the catalyst, γ,δ-disubstituted homoallylic alcohols were obtained in good yields with high E-selectivities and enantioselectivities. Transition state analysis revealed that the disfavored transition state suffers from a syn-pentane interaction between the BF3 catalyst and axially oriented α-substituent of the allylboron reagent. Such a syn-pentane interaction is severe enough to overcome the A1,2 allylic strain between the β-methyl group and the α-substituent of the boron reagent that is present in the favored competing transition state. Consequently, the reaction proceeded with equatorial placement of the α-substituent to furnish γ-methyl substituted homoallylic alcohols with high E-selectivity." @default.
- W2939336497 created "2019-04-25" @default.
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- W2939336497 date "2019-08-01" @default.
- W2939336497 modified "2023-10-13" @default.
- W2939336497 title "Enantioselective syntheses of (E)-γ,δ-disubstituted homoallylic alcohols via BF3·OEt2-catalyzed aldehyde allylboration and analysis of the origin of E-selectivity: A1,2 allylic strain vs. syn-pentane interaction" @default.
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- W2939336497 doi "https://doi.org/10.1016/j.tet.2019.04.019" @default.
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