Quality Control of 5,6-Dihydro-2H-pyran-2-one. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 5,6-Dihydro-2H-pyran-2-one, is researched, Molecular C5H6O2, CAS is 3393-45-1, about Catalytic asymmetric borylative aldol reaction of 5,6-dihydro-2H-pyran-2-one and ketones. Author is Zhang, Qi; Jia, Xueshun; Yin, Liang.
A copper(I)-catalyzed asym. borylative aldol reaction of 5,6-dihydro-2H-pyran-2-one and simple ketones (including aromatic ketones and an aliphatic ketone) was disclosed, which afforded a series of chiral diols after an oxidative work-up in moderate yields with moderate to high diastereoselectivity and excellent enantioselectivity [e.g., 2-acetonaphthone + 5,6-dihydro-2H-pyran-2-one + (BPin)2 → I (63%, >20:1 dr, 99% ee) in presence of Cu(MeCN)4PF6, (R,Rp)-TANIAPHOS, NaBARF, iPrOH as proton source and NaOBu-t as base in THF at -50°]. The lactone moiety was easily opened with methanol to generate a chiral triol in moderate yield.
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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI