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Rhodium-catalyzed reductive mannich coupling of vinyl ketones to N-sulfonylimines mediated by hydrogen.
J Org Chem. 2007 Jul 20; 72(15):5843-6.JO

Abstract

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.

Authors+Show Affiliations

Department of Chemistry and Biochemistry, University of Texas at Austin, 1 University Station A5300, Austin, TX 78712-1167, USA.No affiliation info available

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

17583961

Citation

Garner, Susan A., and Michael J. Krische. "Rhodium-catalyzed Reductive Mannich Coupling of Vinyl Ketones to N-sulfonylimines Mediated By Hydrogen." The Journal of Organic Chemistry, vol. 72, no. 15, 2007, pp. 5843-6.
Garner SA, Krische MJ. Rhodium-catalyzed reductive mannich coupling of vinyl ketones to N-sulfonylimines mediated by hydrogen. J Org Chem. 2007;72(15):5843-6.
Garner, S. A., & Krische, M. J. (2007). Rhodium-catalyzed reductive mannich coupling of vinyl ketones to N-sulfonylimines mediated by hydrogen. The Journal of Organic Chemistry, 72(15), 5843-6.
Garner SA, Krische MJ. Rhodium-catalyzed Reductive Mannich Coupling of Vinyl Ketones to N-sulfonylimines Mediated By Hydrogen. J Org Chem. 2007 Jul 20;72(15):5843-6. PubMed PMID: 17583961.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rhodium-catalyzed reductive mannich coupling of vinyl ketones to N-sulfonylimines mediated by hydrogen. AU - Garner,Susan A, AU - Krische,Michael J, Y1 - 2007/06/21/ PY - 2007/6/23/pubmed PY - 2007/9/26/medline PY - 2007/6/23/entrez SP - 5843 EP - 6 JF - The Journal of organic chemistry JO - J Org Chem VL - 72 IS - 15 N2 - 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. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/17583961/Rhodium_catalyzed_reductive_mannich_coupling_of_vinyl_ketones_to_N_sulfonylimines_mediated_by_hydrogen_ L2 - https://doi.org/10.1021/jo070779w DB - PRIME DP - Unbound Medicine ER -