Zhang, Cheng; Li, Hongli; Pei, Chao; Qiu, Lihua; Hu, Wenhao; Bao, Xiaoguang; Xu, Xinfang published the artcile< Selective Vinylogous Reactivity of Carbene Intermediate in Gold-Catalyzed Alkyne Carbocyclization: Synthesis of Indenols>, Category: alcohols-buliding-blocks, the main research area is diazo alkyne nucleophile gold catalyst regioselective regioselective carbocyclization DFT; indenol preparation.
A gold-catalyzed carbocyclization of alkynes with a pendant diazo group that is completed by reaction with a protic nucleophile for the synthesis of indenol derivatives with a tertiary center is described. Mechanistic studies and DFT calculations indicate that the transformation is initiated by a gold-promoted 5-endo-dig carbocyclization to form the key intermediate vinyl gold carbene, which is intercepted by an unprecedented vinylogous addition and followed by external protic nucleophile-assisted protodeauration. Furthermore, in this catalytic alkyne transformation, various nucleophiles, including water, com. available 1°, 2°, and 3° alcs., menthol, D-galactose, cholesterol, steroid, etc., all perform well under these mild conditions to produce the corresponding indenol derivatives in high yields with structural diversity.
ACS Catalysis published new progress about Alkynes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (diazo esters). 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Category: alcohols-buliding-blocks.
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts