247923-45-1Relevant articles and documents
Establishing the concept of aza-[3 + 3] annulations using enones as a key expansion of this unified strategy in alkaloid synthesis
Gerasyuto, Aleksey I.,Ma, Zhi-Xiong,Buchanan, Grant S.,Hsung, Richard P.
, p. 1170 - 1178 (2013)
A successful enone version of an intramolecular aza-[3 + 3] annulation reaction is described here. Use of piperidinium trifluoroacetate salt as the catalyst and toluene as the solvent appears to be critical for a successful annulation. We also demonstrated for the first time that microwave irradiation can accelerate aza-[3 + 3] annulation reactions. An attempt to expand the scope of the enone aza-[3 + 3] annulation was made in the form of propyleine synthesis as a proof of concept. While synthesis of the enone annulation precursor was successfully accomplished, the annulation proved to be challenging and was only modestly successful.
Gold-catalysed cascade rearrangements of ynamide propargyl esters
Heffernan, Stephen J.,Beddoes, James M.,Mahon, Mary F.,Hennessy, Alan J.,Carbery, David R.
supporting information, p. 2314 - 2316 (2013/06/26)
The Au(i)-catalysed rearrangement of propargylic esters formed from an ynamide has been studied. The reaction is facile, and when conducted in the presence of a reactive indole nucleophile, leads to a cascade process whereby γ-indolyl α-acyloxyenamides are formed in good yield and excellent E-stereoselectivity. The Royal Society of Chemistry.
Synthesis and Cycloaromatization of a Cyclic Enyne-Allene Prodrug
Bekele, Tefsit,Brunette, Steven R.,Lipton, Mark A.
, p. 8471 - 8479 (2007/10/03)
A simple and stable cyclic enediynone (4) has been synthesized using an intramolecular Nozaki-Hiyama-Kishi cyclization as the key step. Reaction with a thiolate nucleophile led to rapid cycloaromatization of 4. Trapping experiments using 1,4-cyclohexadien
