Stereoselective Sc(OTf)3-Catalyzed Aldol Reactions of Disubstituted Silyl Enol Ethers of Aldehydes with Acetals

Peter Yong Wang, Itai Massad, Ilan Marek

Research output: Contribution to journalArticlepeer-review

Abstract

Facile and modular access to stereodefined disubstituted aldehyde-derived silyl enol ethers allowed their successful application in a stereoselective aldol reaction affording the products with excellent yields and diastereomeric ratios. The counter-intuitive stereochemical behavior of this Mukaiyama-aldol reaction is accounted for by a non-classical open transition state.

Original languageEnglish
Pages (from-to)12765-12769
Number of pages5
JournalAngewandte Chemie - International Edition
Volume60
Issue number23
DOIs
StatePublished - 1 Jun 2021

Keywords

  • Mukaiyama-aldol reaction
  • acetals
  • enolates
  • scandium
  • selectivity

All Science Journal Classification (ASJC) codes

  • General Chemistry
  • Catalysis

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