100849-70-5Relevant articles and documents
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Wagner,Moore
, p. 1873 (1950)
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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.).
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.