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| Title
| - Rhodium-Catalyzed Reductive Mannich Couplingof Vinyl Ketones to N-Sulfonylimines Mediatedby Hydrogen
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| Abstract
| - Catalytic hydrogenation of methyl vinyl ketone (MVK) andethyl vinyl ketone (EVK) in the presence of N-(o-nitrophenylsulfonyl)imines 8a−13a at ambient pressure with tri-2-furylphosphine-ligated rhodium catalysts enables formationof Mannich products 8b−13b and 8c−13c with moderateto good levels of syn-diastereoselectivity. As revealed by anassay of various N-protecting groups, excellent yields ofreductive Mannich product also are obtained for N-arylimines1a−4a, although diminished levels of syn-diastereoselectivityare observed. Coupling of MVK to imine 8a under adeuterium atmosphere provides deuterio-8b, which incorporates a single deuterium atom at the former enoneβ-position.
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