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Updated: May 26, 2026
Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Construction of tertiary alcohols bearing perfluoroalkyl chains catalyzed by prolinamide-thioureas
1Laboratory of Organic Chemistry, Department of Chemistry, University of Athens, Panepistimiopolis, Athens 15771, Greece. ckokotos@chem.uoa.gr
Abstract:
A systematic study to evaluate the ability of various organocatalysts to catalyze the aldol reaction between acetone and 2,2,2-trifluoromethyl-1-phenylethanone was undertaken. Benchmark organocatalysts failed to catalyze this reaction. However, a prolinamide-thiourea consisting of (S)-prolinamide, (1S,2S)-diphenylethylenediamine, and (S)-di-tert butyl aspartate proved to be an efficient catalyst, providing tertiary alcohols as the products of the reaction between ketones and perfluoroalkyl ketones in high to quantitative yields and high enantioselectivities (up 81% ee) at a catalyst loading of 2 mol %.
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Alcohols can be synthesized from alkyl halides via nucleophilic substitution reactions. The highly polar carbon-halogen bond in the substrate makes halide a good leaving group. The hydroxide ion or water can act as a nucleophile to take the place of halide and form an alcohol. The substitution reactions occur via two different reaction pathways, SN1 or SN2, depending on the nature of carbon attached to the halide.
Primary alcohols are synthesized from primary alkyl halides, and the...
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The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
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02:35Acid-Catalyzed Dehydration of Alcohols to Alkenes
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Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
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