An alternative synthesis of cycloalkyl-substituted CPA catalysts and application in asymmetric protonation reactions

Liam McLean, Allan J. B. Watson*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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Abstract

An alternative synthesis of cycloalkyl-substituted CPA catalysts is reported. A Negishi coupling offers improved yields and purity of the necessary 1,3,5-tri(cycloalkyl)benzenes. Limitations in the use of commercial organozinc reagents have been identified and a robust procedure for the preparation of these reagents is detailed. Similarly, a robust procedure for the key Kumada coupling is also provided. The route is demonstrated by preparation of three different tri(cycloalkyl)aryl-substituted CPAs and the utility of these catalysts in asymmetric protonation reactions is shown.
Original languageEnglish
Pages (from-to)4943-4945
Number of pages4
JournalEuropean Journal of Organic Chemistry
Issue number35
DOIs
Publication statusPublished - 15 Sept 2021

Keywords

  • Asymmetric protonation
  • Brønsted acid
  • Catalysis
  • Cross-coupling
  • Enantioselectivity

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