An Intramolecular Umpolung Cascade Kukhtin-Ramirez Reaction/Michael Addition-Initiated Cyclization: Stereoselective Synthesis of Tetrasubstituted Cyclopropane Fused 1-Indanones.

Herein, we disclose a fascinating highly stereoselective P(NMe2)3 mediated intramolecular deoxygenative umpolung cascade Michael addition-initiated cyclopropanation with a diverse substrate adaptability. This methodology creates a new horizon for expedient access to valuable 6,5,3-fused scaffolds having an all-carbon quaternary stereocenter via Kukhtin-Ramirez (K-R) adduct formation, with excellent diastereoselectivity and yields under metal-free ambient conditions. A few functional group transformations have also been performed successfully. Additionally, an asymmetric catalytic attempt using (R)-(+)-H8-BINOL has delivered good enantioselectivity.

• Publication year

  2023

• Venue

  Organic Letters

• Publication date

  2023-03-15

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/acs.orglett.3c00494PMID 36920108
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

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