Catalytic, Enantioselective Diamination of Alkenes

Zhong Lin Tao, Scott E. Denmark

Research output: Contribution to journalReview articlepeer-review

Abstract

Enantioselective diamination of alkenes represents one of the most straightforward methods to access enantioenriched, vicinal diamines, which are not only frequently encountered in biologically active compounds, but also have broad applications in asymmetric synthesis. Although the analogous dihydroxylation of olefins is well-established, the development of enantioselective olefin diamination lags far behind. Nevertheless, several successful methods have been developed that operate by different reaction mechanisms, including a cycloaddition pathway, a two-electron redox pathway, and a radical pathway. This short review summarizes recent advances and identifies limitations, with the aim of inspiring further developments in this area. 1 Introduction 2 Cycloaddition Pathway 3 Two-Electron Redox Pathway 3.1 Pd(0)/Pd(II) Diamination 3.2 Pd(II)/Pd(IV) Diamination 3.3 I(I)/I(III) Diamination 3.4 Se(II)/Se(IV) Diamination 4 One-Electron Radical Pathway 4.1 Cu-Catalyzed Diamination 4.2 Fe-Catalyzed Diamination 5 Summary and Outlook.

Original languageEnglish (US)
Article numberss-2021-r0324-sr
Pages (from-to)3951-3962
Number of pages12
JournalSynthesis (Germany)
Volume53
Issue number21
DOIs
StatePublished - Nov 3 2021

Keywords

  • asymmetric catalysis
  • olefin diamination
  • radical
  • redox catalysis
  • transition metal
  • vicinal diamines

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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