Efficient synthesis of tertiary α-hydroxy ketones through CO₂-promoted regioselective hydration of propargylic alcohols

Abstract

A CO2-promoted and silver-catalyzed hydration of propargylic alcohols for the efficient synthesis of α-hydroxy ketones has been developed.

α‐Hydroxy Ketones as Masked Ester Donors in Brønsted Base Catalyzed Conjugate Additions to Nitroalkenes

“…Finally, thiourea catalyst C6 [16] proved to be superior in this reactiont o afford ap roduct with 80 % ee (Table1,e ntry 6). Then, the influence of the two Rg roups at Ca of the ketol substrate, which can be readily prepared through the methodr eported by Qi et al from the corresponding alkyne,C O 2 ,a nd simple ketones as starting materials, [17] was examined. Upon moving from 1A (R = Me) to 2A (R = Et) and 3A (R = Ph), there is not much impact on the reactions electivity (compareT able 1, entries 3-5 with 6-8 and9 ).…”

Silver-catalysed reactions of alkynes: recent advances

“…22b Therefore, it is necessary to develop a mild catalyst system to efficiently capture CO 2 and convert it into a variety of chemicals. 314 Interestingly, Jiang and co-workers discovered a different catalytic performance of the CuI/DBU catalyst system, which allowed for a three-component reaction of propargylic alcohols, nitriles and CO 2 to produce highly substituted 3(2H)-furanones; CuI was used to activate the propargylic alcohols and nitriles. 309 In 2013, the heterogeneous catalysts including PS-NHC-Ag(I) and PS-NHC-Cu(I) complexes were synthesized and applied to catalyze the reaction of propargylic alcohols 442 with CO 2 for producing a-methylene cyclic carbonates 446.…”

AgNO3‐Catalysed Intramolecular Cyclization: Access to Functionalized Cyclopentanones and Spiro‐Cyclopentanones

“…Subsequently, in situ generated DBU and AgNO 3 complex activates ynone ( 1 ) via coordination with a triple bond and form intermediate III . Then, intramolecular cyclization reaction between carbanion and activated triple bond in intermediate III form the intermediate IV . Followed by proto‐demetallation from the intermediate IV gives the substituted cyclopentanone 3 with regeneration of the silver complex and DBU for further catalytic cycle …”