Visible light photoredox catalyzed deprotection of 1,3-oxathiolanes
An efficient visible light photoredox catalyzed aerobic deprotection of 1,3-oxathiolanes using organic dye Eosin Y as a photocatalyst is disclosed. The deprotection procedure features the use of a metal-free catalyst, mild conditions, a broad range of substrate scope, and good functional group tolerance. 35 examples were tested under the standard conditions and most of them afforded the deprotected products in modest to high yields.
Selective arylthiolane deprotection by singlet oxygen: A promising tool for sensors and prodrugs
A routine thioketal protecting group reacts rapidly and selectively with singlet oxygen to reveal ketone products in good (aryl 1,3-dithiolane) to excellent (aryl 1,3-oxathiolane) yields. Arylthiolanes are stable to biologically relevant reactive oxygen species and can be used as a light-activated gating mechanism for activating fluorescent sensors or small molecule prodrugs.
Lamb, Brian M.,Barbas, Carlos F.
supporting information
p. 3196 - 3199
(2015/05/27)
Silica-gel supported sulfamic acid (SA/SiO2) as an efficient and reusable catalyst for conversion of ketones into oxathioacetals and dithioacetals
A simple and efficient method for the conversion of carbonyl compounds to oxathioacetals and dithioacetals using SA/SiO2 as an acid catalyst has been achieved. SA/SiO2 is easily recovered from the reaction mixture and can be reused at least 15 times without loss of catalytic activity.
An efficient and chemoselective method for conversion of carbonyl compounds to 1,3-oxathiolanes with 2-mercaptoethanol catalyzed by TiCl 4-montmorillonite
Formation of 1,3-oxathiolanes from aldehydes and ketones using 2-mercaptoethanol in the presence of TiCl4-montmorillonite under mild reaction conditions in excellent yields is described. Chemoselective monothioacetalization of aldehyde in the p
Scandium(III) Triflate as an Efficient and Recyclable Catalyst for Chemoselective Conversion of Carbonyl Compounds to 1,3-Oxathiolanes
A variety of carbonyl compounds can be easily and rapidly converted to the corresponding 1,3-oxathiolanes in the presence of a catalytic amount of scandium(III) triflate [Sc(OTf)3] in CH2Cl2. After completion of the reacti
Karimi, Babak,Ma'mani, Leila
p. 2503 - 2506
(2007/10/03)
Zirconium tetrachloride (ZrCl4) as an efficient and chemoselective catalyst for conversion of carbonyl compounds to 1,3-oxathiolanes
Different types of aldehydes and ketones can be efficiently converted into their corresponding 1,3-oxathiolanes using 2-mercaptoethanol (1.5-3.2 equiv.) in the presence of catalytic amount (0.04-0.15 equiv.) of ZrCl4 in CH2Cl2/
Karimi, Babak,Seradj, Hassan
p. 805 - 806
(2007/10/03)
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