Lewis acid-mediated reactions of donor-acceptor cyclopropanes with diazo esters
- Authors: Novikov R.A.1, Borisov D.D.1, Tomilov Y.V.1
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Affiliations:
- N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
- Issue: Vol 67, No 2 (2018)
- Pages: 265-273
- Section: Full Articles
- URL: https://journals.rcsi.science/1066-5285/article/view/242123
- DOI: https://doi.org/10.1007/s11172-018-2069-8
- ID: 242123
Cite item
Abstract
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.
About the authors
R. A. Novikov
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: tom@ioc.ac.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991
D. D. Borisov
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: tom@ioc.ac.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991
Yu. V. Tomilov
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Author for correspondence.
Email: tom@ioc.ac.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991