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C1-symmetric versus C2-symmetric ligands in enantioselective copper-bis(oxazoline)-catalyzed cyclopropanation reactions.
Chemistry. 2007; 13(31):8830-9.C

Abstract

A thorough experimental and theoretical study of the enantioselective cyclopropanation of alkenes catalyzed by chiral bis(oxazoline)- and azabis(oxazoline)-copper complexes, which comprise a new family of ligands that lack C2 symmetry, has been conducted. Surprisingly high enantioselectivities were observed with some of these ligands, which were rationalized on the basis of molecular modeling studies. The course of the asymmetric induction in connection with ligand symmetry and the implications for supported enantioselective catalysts are discussed.

Authors+Show Affiliations

Fraile JM
Departamento de Química Orgánica, ICMA, CSIC-Universidad de Zaragoza and IUCH, Universidad de Zaragoza, Pedro Cerbuna 12, 50009 Zaragoza, Spain.
García JI
No affiliation info available
Gissibl A
No affiliation info available
Mayoral JA
No affiliation info available
Pires E
No affiliation info available
Reiser O
No affiliation info available
Roldán M
No affiliation info available
Villalba I
No affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

17674345

Citation

Fraile, José M., et al. "C1-symmetric Versus C2-symmetric Ligands in Enantioselective Copper-bis(oxazoline)-catalyzed Cyclopropanation Reactions." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 13, no. 31, 2007, pp. 8830-9.
Fraile JM, García JI, Gissibl A, et al. C1-symmetric versus C2-symmetric ligands in enantioselective copper-bis(oxazoline)-catalyzed cyclopropanation reactions. Chemistry. 2007;13(31):8830-9.
Fraile, J. M., García, J. I., Gissibl, A., Mayoral, J. A., Pires, E., Reiser, O., Roldán, M., & Villalba, I. (2007). C1-symmetric versus C2-symmetric ligands in enantioselective copper-bis(oxazoline)-catalyzed cyclopropanation reactions. Chemistry (Weinheim an Der Bergstrasse, Germany), 13(31), 8830-9.
Fraile JM, et al. C1-symmetric Versus C2-symmetric Ligands in Enantioselective Copper-bis(oxazoline)-catalyzed Cyclopropanation Reactions. Chemistry. 2007;13(31):8830-9. PubMed PMID: 17674345.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - C1-symmetric versus C2-symmetric ligands in enantioselective copper-bis(oxazoline)-catalyzed cyclopropanation reactions. AU - Fraile,José M, AU - García,José I, AU - Gissibl,Anja, AU - Mayoral,José A, AU - Pires,Elísabet, AU - Reiser,Oliver, AU - Roldán,Marta, AU - Villalba,Isabel, PY - 2007/8/4/pubmed PY - 2007/8/4/medline PY - 2007/8/4/entrez SP - 8830 EP - 9 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 13 IS - 31 N2 - A thorough experimental and theoretical study of the enantioselective cyclopropanation of alkenes catalyzed by chiral bis(oxazoline)- and azabis(oxazoline)-copper complexes, which comprise a new family of ligands that lack C2 symmetry, has been conducted. Surprisingly high enantioselectivities were observed with some of these ligands, which were rationalized on the basis of molecular modeling studies. The course of the asymmetric induction in connection with ligand symmetry and the implications for supported enantioselective catalysts are discussed. SN - 0947-6539 UR - https://www.unboundmedicine.com/medline/citation/17674345/C1_symmetric_versus_C2_symmetric_ligands_in_enantioselective_copper_bis_oxazoline__catalyzed_cyclopropanation_reactions_ L2 - https://doi.org/10.1002/chem.200700681 DB - PRIME DP - Unbound Medicine ER -