Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 14, Pages 5054-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja900827p
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Funding
- NIH-NIGMS [RO1-GM069445]
- Livingston Endowment
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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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