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Beilstein J. Org. Chem. 2022, 18, 1256–1263, doi:10.3762/bjoc.18.131
Graphical Abstract
Scheme 1: C3–Si bond functionalization of biomass-derived 3-silylated furfural platforms.
Scheme 2: Preparation of 3-silylated 2-furyl carbinols.
Scheme 3: C–Si bond functionalization of 2,3-disubstituted furyl carbinols by 1,4-silyl migration.
Scheme 4: Attempts of C3–Si bond functionalization promoted by intramolecular activation via alkoxide.
Scheme 5: Alkoxide-promoted cyclic siloxane formation from 2-[(3-benzyldimethylsilyl)furyl] carbinol 4c.
Scheme 6: TBAF-promoted cyclic siloxane formation from 2-[(3-benzyldimethylsilyl)furyl] carbinol 4c.
Scheme 7: Pd-catalyzed arylation of 2-[(3-benzyldimethylsilyl)furyl] carbinol 4c.
Scheme 8: Cu-catalyzed allylation and methylation of 2-[(3-benzyldimethylsilyl)furyl] carbinols. aCuI⋅PPh3 (1...
Beilstein J. Org. Chem. 2019, 15, 1107–1115, doi:10.3762/bjoc.15.107
Scheme 1: Previously developed bis-nucleophile/bis-electrophile [3 + 2] annulations.
Scheme 2: Concept: [3 + 2] C–C/C–C vs C–C/O–C bond-forming annulations.
Figure 1: Examples of annulated cylopentanic (top) and furan-based (bottom) substructures in natural products....
Scheme 3: C–C/O–C bond forming annulations with dimethyl 3-oxoglutarate (1a).
Scheme 4: C–C/C–C bond-forming annulations with dimethyl 3-oxoglutarate (1a).
Scheme 5: C–C/C–O bond-forming annulations with various bis-nucleophiles.
Scheme 6: Decarboxylative rearrangement of 4a into 5a.
Scheme 7: Proposed mechanism for the Pd-catalyzed part of the [3 + 2] annulation reaction.
Scheme 8: Proposed mechanism for the temperature dependent cyclization part of the [3 + 2] annulation.