139527-84-7Relevant academic research and scientific papers
Sequential Assembly of Morita-Baylis-Hillman Carbonates and Activated ortho-Vinylbenzaldehydes to Construct Chiral Methanobenzo[7]annulenone Frameworks
Jiang, Bo,Xiao, Ben-Xian,Ouyang, Qin,Liang, Hua-Ping,Du, Wei,Chen, Ying-Chun
, (2019)
The α-regioselective asymmetric [3 + 2] annulation reaction of Morita-Baylis-Hillman carbonates from isatins and activated ortho-vinylbenzaldehyses was developed by the catalysis of a chiral tertiary amine. The sequential N-heterocyclic carbene-mediated intramolecular Stetter reaction was conducted to finally furnish the bridged 5,8-methanobenzo[7]annulen-9-one architectures incorporating a spirooxindole motif with excellent stereoselectivity.
An Unusual Doubly Substituted Product from the Phase-Transfer-Catalyzed Heck Reactions of o-Bromobenzaldehydes with Methyl Acrylate
Meegalla, Sanath K.,Taylor, Nicholas J.,Rodrigo, Russell
, p. 2422 - 2427 (2007/10/02)
The reactions of o-bromobenzaldehydes with methyl acrylate under Heck conditions and with phase-transfer catalysis to yield significant amounts of doubly substituted deformylatet products 1A-E in addition to the expected o-formyl cinnamates 2A-E are reported.X-ray crystallography of one such product (4) established that the bromine was replaced by a propionate and the formyl group by an acrylate residue.Employment of deuterium-labeled substrates showed that the hydrogen atom of the formyl group of the substrate was transferred intramolecularly and regiospecifically to the benzylic carbon of the propionate substituent of the product.A tentative hypothesis is advanced to explain these and other experimental findings.
