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Cu(I)-carbenoid- and Ag(I)-Lewis acid-catalyzed asymmetric intermolecular insertion of alpha-diazo compounds into N-H bonds.
Org Biomol Chem. 2004 Oct 21; 2(20):3044-9.OB

Abstract

Chiral Cu(I)-bisoxazoline- and Cu(I)-PN-complexes were found to catalyze the intermolecular insertion of alpha-diazo compounds into N-H bonds. The insertion reactions proceed with enantioselectivities of up to 28% ee for the different alpha-diazo acetates into one of the N-H bonds of different amines. Analogous chiral Ag(I) complexes were found to give higher enantioselectivities of up to 48% ee, however, lower yields were obtained. There are indications, that the Ag(I)-mediated reactions follow a different reaction mechanism compared to the Cu(I)-catalyzed insertions. It is demonstrated that different alpha-amino acid derivatives can be obtained via this approach in good yields and with low to moderate enantioselectivities. However, the results obtained are the highest asymmetric inductions obtained for an intermolecular N-H insertion via chiral carbene complexes or chiral Lewis acid catalysis.

Authors+Show Affiliations

Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, Aarhus, Denmark.No affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

15480470

Citation

Bachmann, Stephan, et al. "Cu(I)-carbenoid- and Ag(I)-Lewis Acid-catalyzed Asymmetric Intermolecular Insertion of Alpha-diazo Compounds Into N-H Bonds." Organic & Biomolecular Chemistry, vol. 2, no. 20, 2004, pp. 3044-9.
Bachmann S, Fielenbach D, Jorgensen KA. Cu(I)-carbenoid- and Ag(I)-Lewis acid-catalyzed asymmetric intermolecular insertion of alpha-diazo compounds into N-H bonds. Org Biomol Chem. 2004;2(20):3044-9.
Bachmann, S., Fielenbach, D., & Jorgensen, K. A. (2004). Cu(I)-carbenoid- and Ag(I)-Lewis acid-catalyzed asymmetric intermolecular insertion of alpha-diazo compounds into N-H bonds. Organic & Biomolecular Chemistry, 2(20), 3044-9.
Bachmann S, Fielenbach D, Jorgensen KA. Cu(I)-carbenoid- and Ag(I)-Lewis Acid-catalyzed Asymmetric Intermolecular Insertion of Alpha-diazo Compounds Into N-H Bonds. Org Biomol Chem. 2004 Oct 21;2(20):3044-9. PubMed PMID: 15480470.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Cu(I)-carbenoid- and Ag(I)-Lewis acid-catalyzed asymmetric intermolecular insertion of alpha-diazo compounds into N-H bonds. AU - Bachmann,Stephan, AU - Fielenbach,Doris, AU - Jorgensen,Karl Anker, Y1 - 2004/09/28/ PY - 2004/10/14/pubmed PY - 2006/5/17/medline PY - 2004/10/14/entrez SP - 3044 EP - 9 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 2 IS - 20 N2 - Chiral Cu(I)-bisoxazoline- and Cu(I)-PN-complexes were found to catalyze the intermolecular insertion of alpha-diazo compounds into N-H bonds. The insertion reactions proceed with enantioselectivities of up to 28% ee for the different alpha-diazo acetates into one of the N-H bonds of different amines. Analogous chiral Ag(I) complexes were found to give higher enantioselectivities of up to 48% ee, however, lower yields were obtained. There are indications, that the Ag(I)-mediated reactions follow a different reaction mechanism compared to the Cu(I)-catalyzed insertions. It is demonstrated that different alpha-amino acid derivatives can be obtained via this approach in good yields and with low to moderate enantioselectivities. However, the results obtained are the highest asymmetric inductions obtained for an intermolecular N-H insertion via chiral carbene complexes or chiral Lewis acid catalysis. SN - 1477-0520 UR - https://www.unboundmedicine.com/medline/citation/15480470/Cu_I__carbenoid__and_Ag_I__Lewis_acid_catalyzed_asymmetric_intermolecular_insertion_of_alpha_diazo_compounds_into_N_H_bonds_ L2 - https://doi.org/10.1039/b412053a DB - PRIME DP - Unbound Medicine ER -