Lewis acid-mediated reactions of donor-acceptor cyclopropanes with diazo esters Full article
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Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285 |
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| Output data | Year: 2018, Volume: 67, Number: 2, Pages: 265-273 Pages count : 9 DOI: 10.1007/s11172-018-2069-8 | ||
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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.
Cite:
Novikov R.A.
, Borisov D.D.
, Tomilov Y.V.
Lewis acid-mediated reactions of donor-acceptor cyclopropanes with diazo esters
Russian Chemical Bulletin. 2018. V.67. N2. P.265-273. DOI: 10.1007/s11172-018-2069-8 WOS Scopus OpenAlex
Lewis acid-mediated reactions of donor-acceptor cyclopropanes with diazo esters
Russian Chemical Bulletin. 2018. V.67. N2. P.265-273. DOI: 10.1007/s11172-018-2069-8 WOS Scopus OpenAlex
Identifiers:
| ≡ Web of science: | WOS:000431320200012 |
| ≡ Scopus: | 2-s2.0-85046551077 |
| ≡ OpenAlex: | W2802011711 |