118741-66-5Relevant articles and documents
Synthesis of New γ-Lactams with gem-Difluorinated Side Chains
Boustie, Jo?l,Gouault, Nicolas,Greé, René,Hachem, Ali,Justaud, Frédéric,Roisnel, Thierry,Soulieman, Ali
supporting information, p. 2258 - 2262 (2019/12/11)
A short and efficient approach has been designed for the synthesis of new γ-lactams that feature gem-difluorinated side-chains in position 4. The key steps involve 1,4-addition of nitroalkane anions on electrophilic gem-difluoroalkenes, followed by a cascade nitro reduction-heterocyclization. This flexible strategy also allows easy introduction of substituents in positions 3 or 5.
Synthesis of γ-acetoxy β-keto esters through regioselective hydration of γ-acetoxy-α,β-alkynoates
Pradhan, Tapas R.,Mendhekar, Kishor L.,Mohapatra, Debendra K.
, p. 5517 - 5531 (2015/06/16)
The Au(I)-catalyzed regioselective hydration of γ-acetoxy-α,β-acetylinic ester by the assistance of a neighboring carbonyl group has been developed. Varieties of simple primary, secondary, and tertiary γ-acetoxy-α,β-acetylinic esters, even those bearing sensitive functional group in the remote reaction sites, are selectively hydrated to the corresponding β-keto esters. The reaction tolerates a wide variety of other carboxylates, such as benzoates, propionates, acrylates, and pivalates, including chiral carboxylates with retention of the configuration. The broad substrate scope, including the derivatization of complex natural products and neutral and open air conditions, makes this atom economical approach very practical. 18O labeling experiments disclose that the oxygen transposition occurs from the carboxylate group to the triple bond, not from water.
Synthesis of fluorenone and anthraquinone derivatives from aryl- and aroyl-substituted propiolates
Puenner, Florian,Schieven, Justin,Hilt, Gerhard
supporting information, p. 4888 - 4891 (2013/10/08)
Fluorenone derivatives were generated from aryl-substituted propiolates via a cobalt-catalyzed Diels-Alder reaction/DDQ-oxidation and Friedel-Crafts-type cyclization. Several functional groups are tolerated, and good to excellent overall yields (up to 89%) could be achieved. For the synthesis of anthraquinone derivatives, aroyl-substituted propiolates were applied in a zinc iodide catalyzed Diels-Alder reaction with 1,3-dienes. The subsequent DDQ oxidation and Friedel-Crafts-type cyclization led to symmetrical as well as some unsymmetrical anthraquinones in good to excellent yields of up to 87% over the three-step reaction sequence.
