Ruthenium-catalyzed C-C coupling of amino alcohols with dienes via transfer hydrogenation: Redox-triggered imine addition and related hydroaminoalkylations

Te Yu Chen, Ryosuke Tsutsumi, T. Patrick Montgomery, Ivan Volchkov, Michael J. Krische

Research output: Contribution to journalArticlepeer-review

50 Citations (Scopus)

Abstract

Ruthenium-catalyzed hydrogen transfer from 4-aminobutanol to butadiene results in the pairwise generation of 3,4-dihydro-2H-pyrrole and an allylruthenium complex, which combine to form products of imine anti-crotylation. In couplings of 1-substituted-1,3-dienes, novel C2 regioselectivity is observed. As corroborated by deuterium labeling studies, kinetically preferred hydrometalation of the terminal olefin of the 1-substituted-1,3-diene delivers a 1,1-disubstituted π-allylruthenium complex that isomerizes to a thermodynamically more stable monosubstituted π-allylruthenium complex, which undergoes imine addition with allylic inversion through a closed transition structure. Direct ruthenium-catalyzed diene hydroaminoalkylations with pyrrolidine also are described.

Original languageEnglish
Pages (from-to)1798-1801
Number of pages4
JournalJournal of the American Chemical Society
Volume137
Issue number5
DOIs
Publication statusPublished - 2015 Feb 11
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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