Phosphine-Promoted Tandem Intermolecular Diels-Alder Reactions with Pentadienyl 4-Nitrobenzoate as a Diene Precursor.

Autor: Zhang L; School of Food and Biological Engineering, Hefei University of Technology, 485 Danxia Road, Hefei, 230601, P. R. China., Liu Y; School of Food and Biological Engineering, Hefei University of Technology, 485 Danxia Road, Hefei, 230601, P. R. China., Li CX; School of Food and Biological Engineering, Hefei University of Technology, 485 Danxia Road, Hefei, 230601, P. R. China., Zhu L; Hubei Key Laboratory of Quality Control of Characteristic Fruits and Vegetables, School of Chemistry and Materials Science, Hubei Engineering University, Xiaogan, 432000, P. R. China., Xiong GY; School of Food and Biological Engineering, Hefei University of Technology, 485 Danxia Road, Hefei, 230601, P. R. China., Fan SL; School of Food and Biological Engineering, Hefei University of Technology, 485 Danxia Road, Hefei, 230601, P. R. China., Dai JJ; School of Food and Biological Engineering, Hefei University of Technology, 485 Danxia Road, Hefei, 230601, P. R. China., Xiao H; School of Food and Biological Engineering, Hefei University of Technology, 485 Danxia Road, Hefei, 230601, P. R. China.; Hubei Key Laboratory of Quality Control of Characteristic Fruits and Vegetables, School of Chemistry and Materials Science, Hubei Engineering University, Xiaogan, 432000, P. R. China.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2023 Sep 08; Vol. 25 (35), pp. 6506-6510. Date of Electronic Publication: 2023 Aug 25.
DOI: 10.1021/acs.orglett.3c02209
Abstrakt: A phosphine-promoted tandem Diels-Alder reaction using pentadienyl 4-nitrobenzoate (α-vinyl MBH adduct) as a diene precursor with 3-olefinic oxindoles or CF 3 -activated ketones as dienophiles has been developed. The reaction proceeds through the formation of a pentadienyl phosphonium intermediate via S N 2'' addition, which acts as both a D-A diene and a precursor for the exomethylene moiety. This method offers a metal-free and step-efficient approach for synthesizing exomethylene-bearing spirooxindoles and dihydropyrans, which are privileged structures found in natural products.
Databáze: MEDLINE
Externí odkaz: