4.7 Article

SnCl4-Promoted [3+2] Annulation of γ-Butyrolactone-Fused Donor-Acceptor Cyclopropanes with Nitriles: Access to γ-Butyrolactone-Fused 1-Pyrrolines

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 13, Pages 8782-8787

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01155

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Funding

  1. Science and Engineering Research Board (SERB), India
  2. University Grants Commission (UGC)

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The [3+2] annulation of gamma-butyrolactone-fused donor-acceptor cyclopropanes with nitriles has been explored for the access of gamma-butyrolactone-fused 1-pyrrolines. The annulation was promoted by tin(IV) chloride, and the products were obtained as single diastereomers in moderate to good yields. The products were synthetically important, and a couple of them were subjected to tandem reductive ring opening/cyclization to give the respective gamma-butyrolactone-fused gamma-butyrolactams in good yields.

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