100849-70-5Relevant academic research and scientific papers
Neighboring Carbonyl Group Assisted Oxyacetoxylation of Propargylic Carboxylates with Retention of Chirality under Metal Free Condition
Pradhan, Tapas R.,Mohapatra, Debendra K.
, p. 3605 - 3611 (2019/07/04)
A metal-free oxyacetoxylation method of primary, secondary and tertiary propargylic carboxylates with retention of chirality was presented. The reaction proceeds through the intramolecular nucleophilic attack of the neighboring carbonyl group on an alkynyliodonium intermediate. The process is general with broad substrate scope and is amenable for application to a variety of propargyl carboxylates including those obtained from natural products. Insight into the mechanistic pathway by isotopic labelling (using H2O18 and D2O) and controlled experiments confirmed. (Figure presented.).
Synthesis of α-Acyloxy-α′-hydroxy Ketones via Cyclic Carbonate Intermediates Generated from Tertiary Bromopropargylic Alcohols and Cs2CO3
Shemyakina, Olesya A.,Volostnykh, Ol'ga G.,Stepanov, Anton V.,Ushakov, Igor' A.
supporting information, p. 7117 - 7121 (2019/11/16)
A facile approach towards α-acyloxy-α′-hydroxy ketones by reaction of readily available tertiary bromopropargylic alcohols and carboxylic acids in system Cs2CO3/H2O/DMF (50–55 °C, 4 h) was developed. Key intermediates of this synthesis are cyclic carbonates generated in situ from bromopropargylic alcohols and Cs2CO3 which have been utilized as both reagent and base promoter.
HYPERVALENT IODINE OXIDATION OF ETHYNYLCARBINOLS: A SHORT AND EFFICIENT CONVERSION OF DIHYDROXYACETONYL GROUPS FROM KETO GROUPS
Kita, Yasuyuki,Yakura, Takayuki,Terashi, Hiroaki,Haruta, Jun-ichi,Tamura, Yasumitsu
, p. 891 - 894 (2007/10/02)
Oxidation of ethynylcarbinols (4a-g), prepared easily from ketones, with a hypervalent iodine reagent, phenyliodosyl bis(trifluoroacetate) (PIFA), in chloroform-acetonitrile-water gave the dihydroxyacetonyl compounds (6a-g) in high yields.Keywords: phenyliodosyl bis(trifluoroacetate); ethynylcarbinol; dihydroxyacetone; terminal alkyne; α-hydroxyketone
CHEMISTRY OF DIHYDRO-1,4-DIOXIN III. A NEW METHOD FOR THE PREPARATION OF α,α'-DIHYDROXY KETONES FROM KETONES AND ALDEHYDES
Fetizon, Marcel,Goulaouic, Pierre,Hanna, Issam
, p. 4925 - 4928 (2007/10/02)
Title compounds, 7, were prepared from ketones and aldehydes via the intermediate 3 by methanolic peracid epoxidation followed by NaBH4 reduction and acidic hydrolysis.Application of this method to the preparation of the unnatural corticoid side chain was reported.
AN EFFICIENT CONVERSION OF KETO GROUPS INTO DIHYDROXYACETONE GROUPS: OXIDATION OF ETHYNYLCARBINOL INTERMEDIATES BY USING HYPERVALENT IODINE REAGENT
Tamura, Yasumitsu,Yakura, Takayuki,Haruta, Jun-ichi,Kita, Yasuyuki
, p. 3837 - 3840 (2007/10/02)
A short and efficient synthesis of dihydroxyacetone groups from keto groups involving the oxidation of ethynylcarbinol intermediates with benzene (PIFA), is described.
