94034-66-9Relevant academic research and scientific papers
Task-specific ionic liquid and CO2-cocatalysed efficient hydration of propargylic alcohols to α-hydroxy ketones
Zhao, Yanfei,Yang, Zhenzhen,Yu, Bo,Zhang, Hongye,Xu, Huanjun,Hao, Leiduan,Han, Buxing,Liu, Zhimin
, p. 2297 - 2301 (2015)
The hydration of propargylic alcohols is a green route to synthesize α-hydroxy ketones. Herein a CO2-reactive ionic liquid (IL), [Bu4P][Im], was found to display high performance for catalyzing the hydration of propargylic alcohols in the presence of atmospheric CO2, and a series of propargylic alcohols could be converted into the corresponding α-hydroxy ketones in good to excellent yields. In the IL/CO2 reaction system, CO2 served as a cocatalyst by forming α-alkylidene cyclic carbonates with propargylic alcohols, and was released via the rapid hydrolysis of the carbonates catalysed by the IL. This is the first example of the efficient hydration of propargylic alcohols under metal-free conditions. This journal is
α-Hydroxy Ketones as Masked Ester Donors in Br?nsted Base Catalyzed Conjugate Additions to Nitroalkenes
Olaizola, Iurre,Campano, Teresa E.,Iriarte, Igor,Vera, Silvia,Mielgo, Antonia,García, Jesús M.,Odriozola, José M.,Oiarbide, Mikel,Palomo, Claudio
, p. 3893 - 3901 (2018/03/21)
The catalyst-controlled enantioselective direct addition reaction of enolizable esters and related carboxylic acid derivatives to π electrophiles remains a difficult synthetic transformation. In this study, the suitability of α-hydroxy ketones as ester equivalents capable of being activated by bifunctional Br?nsted base catalysts in the context of conjugate addition reactions to nitroolefins is demonstrated. The scope of the reaction, which affords the corresponding Michael adducts with very high stereoselectivity (diastereomeric ratio (d.r.) ≥95:5, up to 99 % enantiomeric excess (ee)), and its limitations are explored, as is the aftermath elaboration of adducts into densely functionalized enantioenriched products.
Efficient synthesis of tertiary α-hydroxy ketones through CO 2-promoted regioselective hydration of propargylic alcohols
He, Haitao,Qi, Chaorong,Hu, Xiaohan,Guan, Yuqi,Jiang, Huanfeng
supporting information, p. 3729 - 3733 (2014/08/05)
A carbon dioxide-promoted and silver acetate-catalyzed hydration of propargylic alcohols for the efficient synthesis of tertiary α-hydroxy ketones has been developed. The reaction is proposed to proceed via a tandem process of carbon dioxide incorporation into propargylic alcohols and subsequent hydrolysis. This journal is the Partner Organisations 2014.
A novel aldol condensation alternative: α,β-unsaturated aldehydes from 3-hydroxy-1-alkynes via dihydrodioxepins
Wei, Heng-Xu,Schlosser, Manfred
, p. 1738 - 1743 (2007/10/03)
The controlled aldol condensation between an aliphatic ketone and an acetaldehyde equivalent remains a challenge. One solution to this evergreen problem consists of the nucleophilic addition of acetylene to the ketone and the subsequent isomerization of the resulting 3-hydroxy-1-alkyne to the corresponding 2-alkenal. So far, however, the latter Step could only be executed with acid-insensitive substrates. We now present a milder, three-step method which extends the scope of the procedure considerably. In the first step, the 3-hydroxy-1-alkynes are converted into 2-propynyl ethylene glycol monoethers; these then undergo base-catalyzed cyclization to give the dihydro-1,4-dioxepins, which are hydrolyzed in acidic medium in the third and final step.
Dioxolanones as Synthetic Intermediates. Part 1. Synthesis of α-Keto Acids, α-Keto Aldehydes, and α-Ketols
Ramage, Robert,Griffiths, Gareth J.,Shutt, Fiona E.,Sweeney, John N. A.
, p. 1531 - 1537 (2007/10/02)
2,2-Pentamethylene-1,3-dioxolan-4-one (10) has been elaborated to provide 5'-ylidene derivatives using a Wittig approach.This apparently novel class of compounds is subject to nucleophilic attack at the 4-position because of strain inherent in the 5-membered ring.Thus alkaline hydrolysis leads to the formation of α-keto acids; hydride reduction of dioxolanones incorporating conjugated aryl substituents using di-isobutylaluminium hydride leads to α-keto-aldehydes; the reaction of dioxolanone (15) with methylmagnesium iodide gave the α-ketol (40).
