Silylative Reductive Amination of α,β-Unsaturated Aldehydes: A Convenient Synthetic Route to β-Silylated Secondary Amines

Eunae Kim, Sehoon Park*, Sukbok Chang

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

Described here is a reductive amination/hydrosilylation cascade of α,β-unsaturated aldehydes mediated by a Lewis acidic borane catalyst. The present reaction system provides an one-pot synthetic route towards β-silylated secondary amines that have not been accessible by other previous catalysis. Comparative 1H NMR studies on the silylative reduction of enimines revealed that steric bulkiness of primary amine reactants strongly affects both catalytic efficiency and regioselectivity. This strategy was applicable to a broad range of substrates and amenable to one-pot gram-scale synthesis. Moreover, a diastereoselective introduction of the β-silyl group was also found to be feasible (d.r. up to 71:29).

Original languageEnglish
Pages (from-to)5765-5769
Number of pages5
JournalChemistry - A European Journal
Volume24
Issue number22
DOIs
StatePublished - 17 Apr 2018
Externally publishedYes

Keywords

  • hydrosilylation
  • Lewis acidic borane
  • reductive amination
  • selectivity
  • α,β-unsaturated compounds

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