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Catalytic addition of metallo-aldehyde enolates to ketones: a new C-C bond-forming hydrogenation.
Org Lett. 2004 Mar 04; 6(5):691-4.OL

Abstract

The first catalytic cross-aldolization of metallo-aldehyde enolates with ketone acceptors is enabled via hydrogenation of keto-enals with cationic rhodium catalysts. These results, in conjunction with prior studies involving the catalytic hydrogen-mediated reductive coupling of enones, dienes, and diynes with carbonyl acceptors, support the feasibility of developing a broad new class of catalytic C-C bond formations based on the electrophilic trapping of hydrogenation intermediates. [reaction: see text]

Authors+Show Affiliations

Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, TX 78712, USA.No affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

14986951

Citation

Koech, Phillip K., and Michael J. Krische. "Catalytic Addition of Metallo-aldehyde Enolates to Ketones: a New C-C Bond-forming Hydrogenation." Organic Letters, vol. 6, no. 5, 2004, pp. 691-4.
Koech PK, Krische MJ. Catalytic addition of metallo-aldehyde enolates to ketones: a new C-C bond-forming hydrogenation. Org Lett. 2004;6(5):691-4.
Koech, P. K., & Krische, M. J. (2004). Catalytic addition of metallo-aldehyde enolates to ketones: a new C-C bond-forming hydrogenation. Organic Letters, 6(5), 691-4.
Koech PK, Krische MJ. Catalytic Addition of Metallo-aldehyde Enolates to Ketones: a New C-C Bond-forming Hydrogenation. Org Lett. 2004 Mar 4;6(5):691-4. PubMed PMID: 14986951.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Catalytic addition of metallo-aldehyde enolates to ketones: a new C-C bond-forming hydrogenation. AU - Koech,Phillip K, AU - Krische,Michael J, PY - 2004/2/28/pubmed PY - 2004/6/25/medline PY - 2004/2/28/entrez SP - 691 EP - 4 JF - Organic letters JO - Org Lett VL - 6 IS - 5 N2 - The first catalytic cross-aldolization of metallo-aldehyde enolates with ketone acceptors is enabled via hydrogenation of keto-enals with cationic rhodium catalysts. These results, in conjunction with prior studies involving the catalytic hydrogen-mediated reductive coupling of enones, dienes, and diynes with carbonyl acceptors, support the feasibility of developing a broad new class of catalytic C-C bond formations based on the electrophilic trapping of hydrogenation intermediates. [reaction: see text] SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/14986951/Catalytic_addition_of_metallo_aldehyde_enolates_to_ketones:_a_new_C_C_bond_forming_hydrogenation_ L2 - https://doi.org/10.1021/ol030136c DB - PRIME DP - Unbound Medicine ER -