Three-Component Synthesis of Substituted Perhydropyrans from β-Styrylmalonates, Aldehydes, and Alkoxyaluminum Dichlorides
作者:Denis D. Borisov、Roman A. Novikov、Yury V. Tomilov
DOI:10.1021/acs.orglett.3c04097
日期:2024.2.9
A three-component synthesis of substituted dimethyl dihydro-2H-pyran-3,3(4H)-dicarboxylates in up to 80% yields by the reaction of β-styrylmalonates with aromatic or aliphatic aldehydes in the presence of ROAlCl2 prepared in advance either by exposure of EtAlCl2 with air access or by mixing equimolar amounts of AlCl3 with a primary or secondary alcohol has been developed. If EtAlCl2, itself, is used
通过 β-苯乙烯基丙二酸酯与芳香族或脂肪族醛在 ROAlCl 2存在下反应,三组分合成取代的二氢-2H-吡喃-3,3( 4H )-二羧酸二甲酯,产率高达 80%已经开发出通过将 EtAlCl 2与空气接触或通过将等摩尔量的 AlCl 3与伯醇或仲醇混合来推进。如果使用EtAlCl 2本身,则根本不会形成二氢-2H-吡喃-3,3( 4H )-二酯,而苯乙烯基丙二酸酯通过(4+2)-成环型二聚得到取代的四氢萘的过程是主要流程。首次证明了在具有 α-CH-官能化的环加成反应中使用二氯化烷氧基铝的 CH-O-Al 片段的可能性。