102975-20-2Relevant academic research and scientific papers
Enantioselective Lactonization by π-Acid-Catalyzed Allylic Substitution: A Complement to π-Allylmetal Chemistry
Aponick, Aaron,Kizhakkayil Mangadan, Arun Raj,Liu, Ji
supporting information, p. 22224 - 22229 (2021/09/09)
Asymmetric allylic alkylation (AAA) is a powerful method for the formation of highly useful, non-racemic allylic compounds. Here we present a complementary enantioselective process that generates allylic lactones via π-acid catalysis. More specifically, a
A comparative Study of the Decomposition of o-Alkynyl-Substituted Aryl Diazo Ketones. Synthesis of Polysubstituted β-Naphthols via Arylketene Intermediates
Padwa, Albert,Chiacchio, Ugo,Fairfax, David J.,Kassir, Jamal J.,Litrico, Angelo,at al.
, p. 6429 - 6437 (2007/10/02)
The photochemical, thermal, and rhodium-catalyzed decomposition reactions of several closely related o-alkynyl or o-alkenyl α-diazoaceto- and propiophenone derivatives have been studied.The reaction outcome is markedly dependent upon the reaction conditions employed for nitrogen extrusion.Thermolysis or photolysis of o-alkynyl α-diazopropiophenone derivatives yields polysubstituted β-naphthols.These products are derived from Wolff rearrangement of the initially formed carbene to give an aryl ketene which undergoes intramolecular cyclization onto the o-alkynylsubstituent.In direct contrast to the thermal and photochemical results, Rh(II)-catalyzed decomposition yields products derived from direct attack of a rhodium carbenoid onto the tethered ?-system producing a vinyl carbenoid intermediate.Further reaction of the cyclized carbenoid with the starting diazo compound furnished a vinyl indenone which undergoes a rapid intramolecular Diels-Alder reaction to produce a novel dimer whose structure was elucidated by an X-ray crystal analysis.Replacement of the methyl group on the diazo center with a sterically less demanding hydrogen atom was also found to play an important role in controlling the outcome of the Rh(II)-catalyzed reaction.
