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  • Title: anti-Aminoallylation of aldehydes via ruthenium-catalyzed transfer hydrogenative coupling of sulfonamido allenes: 1,2-aminoalcohols.
    Author: Skucas E, Zbieg JR, Krische MJ.
    Journal: J Am Chem Soc; 2009 Apr 15; 131(14):5054-5. PubMed ID: 19317402.
    Abstract:
    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-d(8) 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 allenes 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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