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Highly enantioselective and diastereoselective 1,3-dipolar cycloaddition reactions between azomethine imines and 3-acryloyl-2-oxazolidinone catalyzed by binaphthyldiimine-Ni(II) complexes.
Org Lett. 2007 Jan 04; 9(1):97-100.OL

Abstract

[reaction: see text] We have found the first example of high levels of asymmetric induction (97-74% ee) along with high diastereoselectivity (>99:1-64:36) in dipole-HOMO-/dipolarophile-LUMO-controlled asymmetric 1,3-dipolar cycloaddition reactions between fused azomethine imines and 3-acryloyl-2-oxazolidinone using a chiral BINIM-Ni(II) complex as a chiral Lewis acid catalyst.

Authors+Show Affiliations

Suga H
Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University, Wakasato, Nagano 380-8553, Japan. sugahio@shinshu-u.ac.jp
Funyu A
No affiliation info available
Kakehi A
No affiliation info available

MeSH

Azo CompoundsCatalysisIminesLigandsModels, MolecularMolecular StructureNickelOrganometallic CompoundsOxazoloneStereoisomerismThiosemicarbazones

Pub Type(s)

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

Language

eng

PubMed ID

17192094

Citation

Suga, Hiroyuki, et al. "Highly Enantioselective and Diastereoselective 1,3-dipolar Cycloaddition Reactions Between Azomethine Imines and 3-acryloyl-2-oxazolidinone Catalyzed By binaphthyldiimine-Ni(II) Complexes." Organic Letters, vol. 9, no. 1, 2007, pp. 97-100.
Suga H, Funyu A, Kakehi A. Highly enantioselective and diastereoselective 1,3-dipolar cycloaddition reactions between azomethine imines and 3-acryloyl-2-oxazolidinone catalyzed by binaphthyldiimine-Ni(II) complexes. Org Lett. 2007;9(1):97-100.
Suga, H., Funyu, A., & Kakehi, A. (2007). Highly enantioselective and diastereoselective 1,3-dipolar cycloaddition reactions between azomethine imines and 3-acryloyl-2-oxazolidinone catalyzed by binaphthyldiimine-Ni(II) complexes. Organic Letters, 9(1), 97-100.
Suga H, Funyu A, Kakehi A. Highly Enantioselective and Diastereoselective 1,3-dipolar Cycloaddition Reactions Between Azomethine Imines and 3-acryloyl-2-oxazolidinone Catalyzed By binaphthyldiimine-Ni(II) Complexes. Org Lett. 2007 Jan 4;9(1):97-100. PubMed PMID: 17192094.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Highly enantioselective and diastereoselective 1,3-dipolar cycloaddition reactions between azomethine imines and 3-acryloyl-2-oxazolidinone catalyzed by binaphthyldiimine-Ni(II) complexes. AU - Suga,Hiroyuki, AU - Funyu,Akira, AU - Kakehi,Akikazu, PY - 2006/12/29/pubmed PY - 2007/2/21/medline PY - 2006/12/29/entrez SP - 97 EP - 100 JF - Organic letters JO - Org Lett VL - 9 IS - 1 N2 - [reaction: see text] We have found the first example of high levels of asymmetric induction (97-74% ee) along with high diastereoselectivity (>99:1-64:36) in dipole-HOMO-/dipolarophile-LUMO-controlled asymmetric 1,3-dipolar cycloaddition reactions between fused azomethine imines and 3-acryloyl-2-oxazolidinone using a chiral BINIM-Ni(II) complex as a chiral Lewis acid catalyst. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/17192094/Highly_enantioselective_and_diastereoselective_13_dipolar_cycloaddition_reactions_between_azomethine_imines_and_3_acryloyl_2_oxazolidinone_catalyzed_by_binaphthyldiimine_Ni_II__complexes_ L2 - https://doi.org/10.1021/ol062675y DB - PRIME DP - Unbound Medicine ER -