Lewis acid-mediated reactions of donor-acceptor cyclopropanes with diazo esters

被引：0
|
作者：
R. A. Novikov
D. D. Borisov
Yu. V. Tomilov
机构：
[1] Russian Academy of Sciences,N. D. Zelinsky Institute of Organic Chemistry
来源：
Russian Chemical Bulletin | 2018年 / 67卷
关键词：
donor-acceptor cyclopropanes; diazo esters; Lewis acids; C—C bond formation;
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摘要：
The reactions of diazo esters with 2-arylcyclopropane-1,1-dicarboxylates, the represen- tatives of donor-acceptor cyclopropanes (DACs), mediated by Sc(OTf)3, SnCl4, and GaCl3 proceeded with nitrogen elimination to give the C—C coupling products. No products of the formal [3+3] cycloaddition of diazo compounds to DACs were formed but the main reaction direction was addition of diazo ester to either 1,3- or 1,2-zwitterions generated upon Lewis acid-mediated cyclopropane ring opening giving rise to new 1,4- and 1,3-zwitterionic inter- mediates. The formed intermediates underwent further fragmentations and rearrangements to give substituted cyclopropanedi-, -tri-, and -tetracarboxylates. Mechanistic aspects of the observed reactions were discussed.
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页码：265 / 273
页数：8
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