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Efficient palladium-catalyzed asymmetric allylic alkylation of ketones and aldehydes.
Org Biomol Chem. 2011 Mar 21; 9(6):1871-5.OB

Abstract

Palladium-catalyzed asymmetric allylic alkylation of ketones, via enamines generated in situ as nucleophiles, were carried out smoothly with chiral metallocene-based P,N-ligands. Under the same conditions, however, reactions of aldehydes could hardly be observed. Subsequently, this obstacle was resolved by using chiral metallocene-based P,P-ligands. Both ketones and aldehydes afforded excellent enantioselectivities with up to 98% ee and 94% ee, respectively.

Authors+Show Affiliations

School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, PR China.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

21283877

Citation

Zhao, Xiaohu, et al. "Efficient Palladium-catalyzed Asymmetric Allylic Alkylation of Ketones and Aldehydes." Organic & Biomolecular Chemistry, vol. 9, no. 6, 2011, pp. 1871-5.
Zhao X, Liu D, Xie F, et al. Efficient palladium-catalyzed asymmetric allylic alkylation of ketones and aldehydes. Org Biomol Chem. 2011;9(6):1871-5.
Zhao, X., Liu, D., Xie, F., Liu, Y., & Zhang, W. (2011). Efficient palladium-catalyzed asymmetric allylic alkylation of ketones and aldehydes. Organic & Biomolecular Chemistry, 9(6), 1871-5. https://doi.org/10.1039/c0ob00915f
Zhao X, et al. Efficient Palladium-catalyzed Asymmetric Allylic Alkylation of Ketones and Aldehydes. Org Biomol Chem. 2011 Mar 21;9(6):1871-5. PubMed PMID: 21283877.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Efficient palladium-catalyzed asymmetric allylic alkylation of ketones and aldehydes. AU - Zhao,Xiaohu, AU - Liu,Delong, AU - Xie,Fang, AU - Liu,Yangang, AU - Zhang,Wanbin, Y1 - 2011/01/31/ PY - 2011/2/2/entrez PY - 2011/2/2/pubmed PY - 2011/4/26/medline SP - 1871 EP - 5 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 9 IS - 6 N2 - Palladium-catalyzed asymmetric allylic alkylation of ketones, via enamines generated in situ as nucleophiles, were carried out smoothly with chiral metallocene-based P,N-ligands. Under the same conditions, however, reactions of aldehydes could hardly be observed. Subsequently, this obstacle was resolved by using chiral metallocene-based P,P-ligands. Both ketones and aldehydes afforded excellent enantioselectivities with up to 98% ee and 94% ee, respectively. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/21283877/Efficient_palladium_catalyzed_asymmetric_allylic_alkylation_of_ketones_and_aldehydes_ L2 - https://doi.org/10.1039/c0ob00915f DB - PRIME DP - Unbound Medicine ER -