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Beilstein J. Org. Chem. 2019, 15, 490–496, doi:10.3762/bjoc.15.42
Graphical Abstract
Figure 1: Structure of most active HPA-12 isomers, originally proposed (1) and revised (2).
Scheme 1: Lipase-catalyzed trans-acylation of (±)-4 and subsequent Mitsunobu inversion. Conditions: (i) Zn/TH...
Scheme 2: Synthesis of azide 9 from (S)-4. Conditions: (i) NaH/Bu4NI/BnBr/THF/25 °C/4 h; (ii) AD-mix-β/t-BuOH...
Scheme 3: Attempted synthesis of 2 from 9. Conditions: (i) (a) LiAlH4 (1 M in THF)/THF/25 °C/3 h, (b) DCC/DMA...
Scheme 4: Actual synthesis of 2 from 9. Conditions: (i) DDQ/CH2Cl2–H2O 4:1/3 h; (ii) a) LiAlH4/THF/25 °C/3 h,...
Beilstein J. Org. Chem. 2018, 14, 2198–2203, doi:10.3762/bjoc.14.193
Scheme 1: Bi-mediated allylation of aldehydes.
Figure 1: Partial 1H NMR spectra (recorded at two temperatures) of the reaction mixture of allyl bromide and ...
Figure 2: Structures of all the possible allylbismuth species.
Scheme 2: Probable reaction mechanism.