Direct Nucleophilic Acylation of Nitroalkenes Promoted by a Fluoride Anion/Thiourea Combination
Journal of the American Chemical Society2006Vol. 128(15), pp. 4932–4933
Citations Over TimeTop 1% of 2006 papers
Abstract
The direct nucleophilic acylation of nitroalkenes is reported utilizing a fluoride-initiated rearrangement of protected thiazolium carbinols. The key combination of fluoride anion and thiourea accesses carbonyl anion reactivity without the use of amine or amide bases typically employed in the generation of these Umpolung nucleophiles. The mild reaction conditions used to generate the reactive carbonyl anion species in situ allow for conjugate additions in good yield to sensitive nitroalkene electrophiles. The process is tolerant of a variety of thiazolium carbinols and nitroalkene substrates and can be rendered enantioselective and diastereoselective by the addition of a chiral thiourea derived from quinine.
Related Papers
- → SF5-Synthons: Pathways to Organic Derivatives of SF6(2005)31 cited
- → Supramolecular Synthons: Will Giant Rigid Superspheres Do?(2016)16 cited
- → A mathematical model of the synthon(1988)11 cited
- → Mathematical Model of Synthon Reactions(1989)1 cited
- → ChemInform Abstract: Ethynylglycine Synthon, a Useful Precursor for the Synthesis of Biologically Active Compounds: an Update ‐ Part I: Preparations of Ethynylglycine Synthon(2015)