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anti-Aminoallylation of Aldehydes via Ruthenium-Catalyzed Transfer Hydrogenative Coupling of Sulfonamido Allenes: 1,2-Aminoalcohols
Skucas, Eduardas
Zbieg, Jason R
Krische, Michael J
Journal of the American Chemical Society, 131(14), pp 5054-+, 2009-4-15
Summary
Ruthenium-catalyzed transfer hydrogenation of N-sulfonamido allene 1e in the presence of aromatic aldehydes 2a-f, alpha,beta-unsaturated aldehydes 2g-i, and aliphatic aldehydes 2j-l results in reductive coupling to furnish the corresponding anti-aminoallylation products 3a-l. Reductive coupling of allenamide 1e to aldehyde 2a conducted using 2-propanol-d8 as the terminal reductant delivers deuterio-3a. The observed pattern of deuterium incorporation suggests reversible allene hydrometalation with incomplete regioselectivity in advance of carbonyl addition. A survey of monosubstituted attenes 1f-i was conducted. High levels of anti-diastereoselectivity were observed only when tert-butyl allene 1f was used. This protocol represents an alternative to the use of amino-substituted allylborane reagents in carbonyl aminoallylation and avoids the use of stoichiometric metallic reagents.
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