Chiral π–Cu(II) Catalysts for the Enantioselective α‑Amination of N‑Acyl-3,5-dimethylpyrazoles
We report the highly enantioselective α-amination of N-acyl-3,5-dimethylpyrazoles with dialkyl azodicarboxylates, catalyzed by in situ generated π–Cu(II) complexes that consist of Cu(OTf)2 and N-(5H-dibenzo[a,d][7]annulen-5-yl)-l-alanine-derived amides, to give the corresponding products as d-α...
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Veröffentlicht in: | Organic letters 2022-10, Vol.24 (41), p.7685-7689 |
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Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | We report the highly enantioselective α-amination of N-acyl-3,5-dimethylpyrazoles with dialkyl azodicarboxylates, catalyzed by in situ generated π–Cu(II) complexes that consist of Cu(OTf)2 and N-(5H-dibenzo[a,d][7]annulen-5-yl)-l-alanine-derived amides, to give the corresponding products as d-α-amino acid derivatives (up to >99% yield and 99% ee). The site-selectivity and enantioselectivity can be satisfactorily explained by the coordination of dialkyl azodicarboxylate with π–Cu(II) complex. The synthetic potential of this one-pot transformation to the α-amino ester is also described. |
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ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/acs.orglett.2c03249 |