Synthesis of homopropargyl alcohols via sonochemical Barbier-type reaction

Easily accessible non-aromatic heterocycles with handles: 4-bromo-2,3-dihydrofurans from 1,2-dibromohomoallylic alcohols

“…Homopropargyl alcohols 5 were readily prepared by zinc-mediated propargylation of the corresponding aldehydes and ketones. 16 These were efficiently converted to E-dibromoalkenes 2 by treatment with CuBr 2 in the presence of activated molecular sieves. 17 Of note, these latter conditions were incompatible with highly electron rich aromatic compounds (e.g., p-MeOPh, thiophene).…”

Gold-Catalyzed Synthesis of Oxygen- and Nitrogen-Containing Heterocycles from Alkynyl Ethers: Application to the Total Synthesis of Andrachcinidine

“…The synthesis of the initial group of substrates is shown in Scheme . Monosilylation of α,ω-diols 3a − c followed by oxidation, Barbier-type propargyl addition, and methylation provided silyl ethers 4a − c . Desilylation yielded substrate 1 and its lower and higher homologues 5 and 6 .…”

2-Vinyl Threoninol Derivatives via Acid-Catalyzed Allylic Substitution of Bisimidates

“…Alcohols 4a , b , e – l were prepared according to literature procedure . These compounds have been previously described in the literature: 1-(furan-3-yl)-2-methylpropan-1-ol ( 4a ), 1-(furan-3-yl)­pentan-1-ol ( 4b ), 1-(furan-3-yl)-2,2-dimethylpropan-1-ol ( 4e ), furan-3-yl­(phenyl)­methanol ( 4f ), , 1-(furan-3-yl)-2-phenylethanol ( 4g ), 1-(furan-3-yl)­ethanol ( 4h ), 1-(furan-3-yl)­but-3-en-1-ol ( 4i ), 1-(furan-3-yl)­pent-4-en-1-ol (11j) , 1-(furan-3-yl)­prop-2-en-1-ol ( 11k ), , 1-(furan-3-yl)­but-3-yn-1-ol ( 11l ) …”

“…16 These compounds have been previously described in the literature: 1-(furan-3-yl)-2-methylpropan-1-ol (4a), 16 1-(furan-3-yl)pentan-1-ol (4b), 17 1-(furan-3-yl)-2,2-dimethylpropan-1-ol (4e), 18 furan-3-yl(phenyl)methanol (4f), 16,18 1-(furan-3-yl)-2-phenylethanol (4g), 18 1-(furan-3-yl)ethanol (4h), 19 1-(furan-3-yl)but-3-en-1-ol (4i), 19 1-(furan-3-yl)pent-4-en-1-ol (11j), 20 1-(furan-3-yl)prop-2-en-1-ol (11k), 18,21 1-(furan-3-yl)but-3-yn-1-ol (11l). 22 (S)-1-(Furan-3-yl)-2-methylpropan-1-ol ((S)-4a). To a solution of racemic alcohol 4a (2.7 g, 19.3 mmol) in dry DCM (100 mL) was added DMP (55 mL, 23.7 mmol), and the reaction mixture was stirred for 6 h at rt.…”