Origin of High Diastereoselectivity in Reactions of Seven-Membered-Ring Enolates

Olga Lavinda, Collin H. Witt, K. A. Woerpel

Research output: Contribution to journalArticlepeer-review

Abstract

Unlike many reactions of their six-membered-ring counterparts, the reactions of chiral seven-membered-ring enolates are highly diastereoselective. Diastereoselectivity was observed for a range of substrates, including lactam, lactone, and cyclic ketone derivatives. The stereoselectivity arises from torsional and steric interactions that develop when electrophiles approach the diastereotopic π-faces of the enolates, which are distinguished by subtle differences in the orientation of nearby atoms of the ring.

Original languageEnglish (US)
Article numbere202114183
JournalAngewandte Chemie - International Edition
Volume61
Issue number14
DOIs
StatePublished - Mar 28 2022

Keywords

  • Conformational Analysis
  • Diastereoselectivity
  • Enolates
  • Seven-Membered-Rings
  • Torsional Strain
  • Carboxylic Acids
  • Ketones
  • Stereoisomerism

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

Fingerprint

Dive into the research topics of 'Origin of High Diastereoselectivity in Reactions of Seven-Membered-Ring Enolates'. Together they form a unique fingerprint.

Cite this