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Enolate generation under hydrogenation conditions: catalytic aldol cycloreduction of keto-enones.
Org Lett. 2003 Apr 03; 5(7):1143-6.OL

Abstract

[reaction: see text] Formal heterolytic activation of elemental hydrogen under Rh catalysis enables the reductive generation of enolates from enones under hydrogenation conditions. Enolates generated in this fashion participate in catalytic C-C bond formation via carbonyl addition to aldehyde and, as demonstrated in this account, ketone partners. Notably, the use of appendant dione partners enables diastereoselective formation of cycloaldol products possessing 3-stereogenic centers, including 2-contiguous quaternary centers.

Authors+Show Affiliations

Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, Texas 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

12659594

Citation

Huddleston, Ryan R., and Michael J. Krische. "Enolate Generation Under Hydrogenation Conditions: Catalytic Aldol Cycloreduction of Keto-enones." Organic Letters, vol. 5, no. 7, 2003, pp. 1143-6.
Huddleston RR, Krische MJ. Enolate generation under hydrogenation conditions: catalytic aldol cycloreduction of keto-enones. Org Lett. 2003;5(7):1143-6.
Huddleston, R. R., & Krische, M. J. (2003). Enolate generation under hydrogenation conditions: catalytic aldol cycloreduction of keto-enones. Organic Letters, 5(7), 1143-6.
Huddleston RR, Krische MJ. Enolate Generation Under Hydrogenation Conditions: Catalytic Aldol Cycloreduction of Keto-enones. Org Lett. 2003 Apr 3;5(7):1143-6. PubMed PMID: 12659594.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enolate generation under hydrogenation conditions: catalytic aldol cycloreduction of keto-enones. AU - Huddleston,Ryan R, AU - Krische,Michael J, PY - 2003/3/28/pubmed PY - 2003/8/26/medline PY - 2003/3/28/entrez SP - 1143 EP - 6 JF - Organic letters JO - Org Lett VL - 5 IS - 7 N2 - [reaction: see text] Formal heterolytic activation of elemental hydrogen under Rh catalysis enables the reductive generation of enolates from enones under hydrogenation conditions. Enolates generated in this fashion participate in catalytic C-C bond formation via carbonyl addition to aldehyde and, as demonstrated in this account, ketone partners. Notably, the use of appendant dione partners enables diastereoselective formation of cycloaldol products possessing 3-stereogenic centers, including 2-contiguous quaternary centers. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/12659594/Enolate_generation_under_hydrogenation_conditions:_catalytic_aldol_cycloreduction_of_keto_enones_ L2 - https://doi.org/10.1021/ol0300219 DB - PRIME DP - Unbound Medicine ER -