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Ilyin A, Kysil V, Krasavin M, et al. Complexity-enhancing acid-promoted rearrangement of tricyclic products of tandem Ugi 4CC/intramolecular Diels-Alder reaction. J Org Chem. 2006;71(25):9544-7doi: 10.1021/jo061825f.
Ilyin, A., Kysil, V., Krasavin, M., Kurashvili, I., & Ivachtchenko, A. V. (2006). Complexity-enhancing acid-promoted rearrangement of tricyclic products of tandem Ugi 4CC/intramolecular Diels-Alder reaction. The Journal of organic chemistry, 71(25), 9544-7. https://doi.org/10.1021/jo061825f
Ilyin, Alexei, et al. "Complexity-enhancing acid-promoted rearrangement of tricyclic products of tandem Ugi 4CC/intramolecular Diels-Alder reaction." The Journal of organic chemistry vol. 71,25 (2006): 9544-7. doi: https://doi.org/10.1021/jo061825f
Ilyin A, Kysil V, Krasavin M, Kurashvili I, Ivachtchenko AV. Complexity-enhancing acid-promoted rearrangement of tricyclic products of tandem Ugi 4CC/intramolecular Diels-Alder reaction. J Org Chem. 2006 Dec 08;71(25):9544-7. doi: 10.1021/jo061825f. PMID: 17137394.
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J Org Chem. 2006 Dec 08;71(25):9544-7. doi: 10.1021/jo061825f.

Complexity-enhancing acid-promoted rearrangement of tricyclic products of tandem Ugi 4CC/intramolecular Diels-Alder reaction.

The Journal of organic chemistry

Alexei Ilyin, Volodymyr Kysil, Mikhail Krasavin, Irina Kurashvili, Alexandre V Ivachtchenko

Affiliations

  1. Chemical Diversity Research Institute, Khimki, Moscow Reg., 114401 Russia.

PMID: 17137394 DOI: 10.1021/jo061825f

Abstract

The unexpected rearrangement of 2,3,7,7a-tetrahydro-3a,6-epoxyisoindol-1-one products of the tandem Ugi 4CC/intramolecular Diels-Alder reaction in 85% H3PO4 was discovered to provide diastereomerically pure tricyclic bislactam lactone-containing natural product-like products in high yield. Mechanistic rationale for the observed rearrangement was proposed and has been tentatively confirmed by additional experiments.

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