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Copper-catalyzed asymmetric conjugate addition of Grignard reagents to trisubstituted enones. Construction of all-carbon quaternary chiral centers.
J Am Chem Soc. 2006 Jul 05; 128(26):8416-7.JA

Abstract

The copper-catalyzed asymmetric conjugate addition of Grignard reagents to trisubstituted cyclic enones affords enantioenriched all-carbon quaternary centers with up to 96% ee. The chiral ligand is a diaminocarbene, directly generated in situ. The combination of Grignard reagent and diaminocarbene is unprecedented in conjugate addition, and the additon of the phenyl group, on such enones, cannot be done by other conjugate addition methods.

Authors+Show Affiliations

Martin D
Département de Chimie Organique, Université de Genève, 30 quai Ernest Ansermet, CH-1211 Genève 4, Switzerland.
Kehrli S
No affiliation info available
d'Augustin M
No affiliation info available
Clavier H
No affiliation info available
Mauduit M
No affiliation info available
Alexakis A
No affiliation info available

MeSH

CatalysisCopperFree RadicalsIndicators and ReagentsKetonesLigandsMolecular StructureOrganometallic CompoundsStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

16802804

Citation

Martin, David, et al. "Copper-catalyzed Asymmetric Conjugate Addition of Grignard Reagents to Trisubstituted Enones. Construction of All-carbon Quaternary Chiral Centers." Journal of the American Chemical Society, vol. 128, no. 26, 2006, pp. 8416-7.
Martin D, Kehrli S, d'Augustin M, et al. Copper-catalyzed asymmetric conjugate addition of Grignard reagents to trisubstituted enones. Construction of all-carbon quaternary chiral centers. J Am Chem Soc. 2006;128(26):8416-7.
Martin, D., Kehrli, S., d'Augustin, M., Clavier, H., Mauduit, M., & Alexakis, A. (2006). Copper-catalyzed asymmetric conjugate addition of Grignard reagents to trisubstituted enones. Construction of all-carbon quaternary chiral centers. Journal of the American Chemical Society, 128(26), 8416-7.
Martin D, et al. Copper-catalyzed Asymmetric Conjugate Addition of Grignard Reagents to Trisubstituted Enones. Construction of All-carbon Quaternary Chiral Centers. J Am Chem Soc. 2006 Jul 5;128(26):8416-7. PubMed PMID: 16802804.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Copper-catalyzed asymmetric conjugate addition of Grignard reagents to trisubstituted enones. Construction of all-carbon quaternary chiral centers. AU - Martin,David, AU - Kehrli,Stefan, AU - d'Augustin,Magali, AU - Clavier,Hervé, AU - Mauduit,Marc, AU - Alexakis,Alexandre, PY - 2006/6/29/pubmed PY - 2007/9/13/medline PY - 2006/6/29/entrez SP - 8416 EP - 7 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 128 IS - 26 N2 - The copper-catalyzed asymmetric conjugate addition of Grignard reagents to trisubstituted cyclic enones affords enantioenriched all-carbon quaternary centers with up to 96% ee. The chiral ligand is a diaminocarbene, directly generated in situ. The combination of Grignard reagent and diaminocarbene is unprecedented in conjugate addition, and the additon of the phenyl group, on such enones, cannot be done by other conjugate addition methods. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/16802804/Copper_catalyzed_asymmetric_conjugate_addition_of_Grignard_reagents_to_trisubstituted_enones__Construction_of_all_carbon_quaternary_chiral_centers_ L2 - https://doi.org/10.1021/ja0629920 DB - PRIME DP - Unbound Medicine ER -