Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 5, Pages 1798-1801Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja5130258
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Funding
- Robert A. Welch Foundation [F-0038]
- NSF [CHE-1265504]
- Center for Green Chemistry and Catalysis
- Uehara Memorial Foundation
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1265504] Funding Source: National Science Foundation
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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 p-allylruthenium complex that isomerizes to a thermodynamically more stable monosubstituted p-allylruthenium complex, which undergoes imine addition with allylic inversion through a closed transition structure. Direct ruthenium-catalyzed diene hydroaminoalkylations with pyrrolidine also are described.
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