Synthesis of γ-, δ-, and ε-Lactams by Asymmetric Transfer Hydrogenation of N-(tert-Butylsulfinyl)iminoesters
Contribuinte(s) |
Universidad de Alicante. Departamento de Química Orgánica Universidad de Alicante. Instituto Universitario de Síntesis Orgánica Catálisis Estereoselectiva en Síntesis Orgánica (CESO) Síntesis Asimétrica (SINTAS) |
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Data(s) |
19/06/2014
19/06/2014
27/03/2013
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Resumo |
Highly enantiomerically enriched γ- and δ-lactams have been prepared by a simple and very efficient procedure that involves the asymmetric transfer hydrogenation of N-(tert-butylsulfinyl)iminoesters followed by desulfinylation of the nitrogen atom and spontaneous cyclization to the desired lactams during the basic workup procedure. Five- and six-membered ring lactams bearing aromatic, heteroaromatic, and aliphatic substituents have been obtained in very high yields and ee’s up to >99%. A slight modification of the procedure also allowed the preparation of ε-lactams in good yields and very high enantioselectivities. Both enantiomers of the final lactams could be prepared with equal efficiency by changing the absolute configuration of the sulfinyl chiral auxiliary. |
Identificador |
Journal of Organic Chemistry. 2013, 78(8): 3647-3654. doi:10.1021/jo400164y 0022-3263 (Print) 1520-6904 (Online) http://hdl.handle.net/10045/38258 10.1021/jo400164y |
Idioma(s) |
eng |
Publicador |
American Chemical Society |
Relação |
http://dx.doi.org/10.1021/jo400164y |
Direitos |
© 2013 American Chemical Society info:eu-repo/semantics/openAccess |
Palavras-Chave | #γ-, δ-, and ε-lactams #Asymmetric transfer hydrogenation #N-(tert-butylsulfinyl)iminoesters #Química Orgánica |
Tipo |
info:eu-repo/semantics/article |