title: Ruthenium-catalyzed C-C coupling of amino alcohols with dienes via transfer hydrogenation: redox-triggered imine addition and related hydroaminoalkylations.
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.
authors: Department of Chemistry, University of Texas at Austin , Austin, Texas 78712, United States.
authors: Te-Yu
authors: TY
authors: Chen
authors: Ryosuke
authors: R
authors: Tsutsumi
authors: T Patrick
authors: TP
authors: Montgomery
authors: Ivan
authors: I
authors: Volchkov
authors: Michael J
authors: MJ
authors: Krische