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Dual palladium- and proline-catalyzed allylic alkylation of enolizable ketones and aldehydes with allylic alcohols.
Org Lett. 2009 Mar 19; 11(6):1453-6.OL

Abstract

The dual Pd/proline-catalyzed alpha-allylation reaction of a variety of enolizable ketones and aldehydes with allylic alcohols is described. In this reaction, the choice of a large-bite angle ligand Xantphos and proline as the organocatalyst was essential for generation of the crucial pi-allyl Pd intermediate from allylic alcohol, followed by nucleophilic attack of the enamine formed in situ from the corresponding enolizable carbonyl substrate and proline.

Authors+Show Affiliations

Institut für Organische Chemie and Biochemie, Freiburg Institute for Advanced Studies, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79104 Freiburg, Germany.No affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

19243116

Citation

Usui, Ippei, et al. "Dual Palladium- and Proline-catalyzed Allylic Alkylation of Enolizable Ketones and Aldehydes With Allylic Alcohols." Organic Letters, vol. 11, no. 6, 2009, pp. 1453-6.
Usui I, Schmidt S, Breit B. Dual palladium- and proline-catalyzed allylic alkylation of enolizable ketones and aldehydes with allylic alcohols. Org Lett. 2009;11(6):1453-6.
Usui, I., Schmidt, S., & Breit, B. (2009). Dual palladium- and proline-catalyzed allylic alkylation of enolizable ketones and aldehydes with allylic alcohols. Organic Letters, 11(6), 1453-6. https://doi.org/10.1021/ol9001812
Usui I, Schmidt S, Breit B. Dual Palladium- and Proline-catalyzed Allylic Alkylation of Enolizable Ketones and Aldehydes With Allylic Alcohols. Org Lett. 2009 Mar 19;11(6):1453-6. PubMed PMID: 19243116.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Dual palladium- and proline-catalyzed allylic alkylation of enolizable ketones and aldehydes with allylic alcohols. AU - Usui,Ippei, AU - Schmidt,Stefan, AU - Breit,Bernhard, PY - 2009/2/27/entrez PY - 2009/2/27/pubmed PY - 2009/4/10/medline SP - 1453 EP - 6 JF - Organic letters JO - Org Lett VL - 11 IS - 6 N2 - The dual Pd/proline-catalyzed alpha-allylation reaction of a variety of enolizable ketones and aldehydes with allylic alcohols is described. In this reaction, the choice of a large-bite angle ligand Xantphos and proline as the organocatalyst was essential for generation of the crucial pi-allyl Pd intermediate from allylic alcohol, followed by nucleophilic attack of the enamine formed in situ from the corresponding enolizable carbonyl substrate and proline. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/19243116/Dual_palladium__and_proline_catalyzed_allylic_alkylation_of_enolizable_ketones_and_aldehydes_with_allylic_alcohols_ L2 - https://doi.org/10.1021/ol9001812 DB - PRIME DP - Unbound Medicine ER -