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Enantioselective addition of cyclic enol silyl ethers to 2-alkenoyl-pyridine-N-oxides catalysed by Cu(II)-bis(oxazoline) complexes.
Chemistry. 2012 Sep 10; 18(37):11662-8.C

Abstract

Asymmetric reactions involving (E)-3-aryl-1-(pyridin-2-yl-N-oxide)prop-2-en-1-ones and cyclic enol silyl ethers show good yields and excellent enantioselectivities (up to 99.9 % ee) when catalysed by bis(oxazoline)-Cu(II) complexes. Different reaction pathways can be followed by different enol silyl ethers: with 2-(trimethylsilyloxy)furan, a Mukaiyama-Michael adduct is obtained, whereas a hetero Diels-Alder cycloadduct was formed by using (1,2-dihydronaphthalen-4-yloxy)trimethylsilane. In the latter reaction, the absolute configuration of the product is consistent with a reagent approach to the less hindered Re face of the coordinated substrate in the reactive complex.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Livieri A
Department of Organic Chemistry, University of Pavia, V. le Taramelli, 10; 27100 Pavia, Italy.
Boiocchi M
No affiliation info available
Desimoni G
No affiliation info available
Faita G
No affiliation info available

MeSH

CatalysisCopperCrystallography, X-RayEthers, CyclicModels, MolecularMolecular StructureOrganometallic CompoundsOxazolesPyridinesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

22847937

Citation

Livieri, Alessandro, et al. "Enantioselective Addition of Cyclic Enol Silyl Ethers to 2-alkenoyl-pyridine-N-oxides Catalysed By Cu(II)-bis(oxazoline) Complexes." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 18, no. 37, 2012, pp. 11662-8.
Livieri A, Boiocchi M, Desimoni G, et al. Enantioselective addition of cyclic enol silyl ethers to 2-alkenoyl-pyridine-N-oxides catalysed by Cu(II)-bis(oxazoline) complexes. Chemistry. 2012;18(37):11662-8.
Livieri, A., Boiocchi, M., Desimoni, G., & Faita, G. (2012). Enantioselective addition of cyclic enol silyl ethers to 2-alkenoyl-pyridine-N-oxides catalysed by Cu(II)-bis(oxazoline) complexes. Chemistry (Weinheim an Der Bergstrasse, Germany), 18(37), 11662-8. https://doi.org/10.1002/chem.201201214
Livieri A, et al. Enantioselective Addition of Cyclic Enol Silyl Ethers to 2-alkenoyl-pyridine-N-oxides Catalysed By Cu(II)-bis(oxazoline) Complexes. Chemistry. 2012 Sep 10;18(37):11662-8. PubMed PMID: 22847937.
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TY - JOUR T1 - Enantioselective addition of cyclic enol silyl ethers to 2-alkenoyl-pyridine-N-oxides catalysed by Cu(II)-bis(oxazoline) complexes. AU - Livieri,Alessandro, AU - Boiocchi,Massimo, AU - Desimoni,Giovanni, AU - Faita,Giuseppe, Y1 - 2012/07/29/ PY - 2012/04/10/received PY - 2012/8/1/entrez PY - 2012/8/1/pubmed PY - 2013/1/9/medline SP - 11662 EP - 8 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 18 IS - 37 N2 - Asymmetric reactions involving (E)-3-aryl-1-(pyridin-2-yl-N-oxide)prop-2-en-1-ones and cyclic enol silyl ethers show good yields and excellent enantioselectivities (up to 99.9 % ee) when catalysed by bis(oxazoline)-Cu(II) complexes. Different reaction pathways can be followed by different enol silyl ethers: with 2-(trimethylsilyloxy)furan, a Mukaiyama-Michael adduct is obtained, whereas a hetero Diels-Alder cycloadduct was formed by using (1,2-dihydronaphthalen-4-yloxy)trimethylsilane. In the latter reaction, the absolute configuration of the product is consistent with a reagent approach to the less hindered Re face of the coordinated substrate in the reactive complex. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/22847937/Enantioselective_addition_of_cyclic_enol_silyl_ethers_to_2_alkenoyl_pyridine_N_oxides_catalysed_by_Cu_II__bis_oxazoline__complexes_ L2 - https://doi.org/10.1002/chem.201201214 DB - PRIME DP - Unbound Medicine ER -