Li, Ting; Cheng, Xinpeng; Qian, Pengcheng; Zhang, Liming published the artcile< Gold-catalysed asymmetric net addition of unactivated propargylic C-H bonds to tethered aldehydes>, HPLC of Formula: 627-27-0, the main research area is chiral fused homopropargylic alc preparation enantioselective density functional theory; propargylic aldehyde intramol addition gold bifunctional phosphine ligand catalyst.
The asym. one-step net addition of unactivated propargylic C-H bonds to aldehydes such as 7-(dimethyl(phenyl)silyl)hept-6-ynal, 4-(benzyloxy)-7-(tert-butyldimethylsilyl)hept-6-ynal, 7-(tert-Butyldimethylsilyl)-2-phenylhept-6-ynal, etc. leads to an atom-economic construction of versatile chiral homopropargylic alcs. e.g., I, but has not yet been realized. Here, implementation in an intramol. manner under mild reaction conditions have been showed. This chem.-via cooperative gold catalysis enabled by chiral bifunctional phosphine ligands (1R/1S)-II (R = Me, Cy; R1 = H, Me)-achieves asym. catalytic deprotonation of propargylic C-H (pKa > 30) by a tertiary amine group (pKa ≈ 10) of the ligand in the presence of much more acidic aldehydic α-hydrogens (pKa ≈ 17). The reaction exhibits a broad scope and readily accommodates various functional groups. The cyclopentane/cyclohexane-fused homopropargylic alc. products e.g., III are formed with excellent enantiomeric excesses and high trans-selectivities with or without a preexisting substrate chiral center. D. functional theory studies of the reaction support the conceived reaction mechanism and the calculated energetics corroborate the observed stereoselectivity and confirm addnl. metal-ligand cooperation.
Nature Catalysis published new progress about Alcohols, chiral Role: PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (homopropargylic-). 627-27-0 belongs to class alcohols-buliding-blocks, and the molecular formula is C4H8O, HPLC of Formula: 627-27-0.
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts