期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 72, 期 15, 页码 5843-5846出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo070779w
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资金
- NIGMS NIH HHS [R01 GM 69445] Funding Source: Medline
Catalytic hydrogenation of methyl vinyl ketone (MVK) and ethyl vinyl ketone (EVK) in the presence of N-(o-nitrophenylsulfonyl)imines 8a-13a at ambient pressure with tri-2-furylphosphine-ligated rhodium catalysts enables formation of Mannich products 8b-13b and 8c-13c with moderate to good levels of syn-diastereoselectivity. As revealed by an assay of various N-protecting groups, excellent yields of reductive Mannich product also are obtained for N-arylimines 1a-4a, although diminished levels of syn-diastereoselectivity are observed. Coupling of MVK to imine 8a under a deuterium atmosphere provides deuterio-8b, which incorporates a single deuterium atom at the former enone beta-position.
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