ABSTRACT: The direct addition of metalated alkoxydiene 2, obtained from R,β-unsaturated acetal 1 through a LIC-KORpromoted conjugated elimination reaction, to enantiopure sulfinimines 3 (both R and S N-sulfinyl imines) afforded Nsulfinyl alkoxydienyl amines 4 with high diastereoselectivity. Functionalized enantiopure alkoxydienyl amines 5 were then easily obtained upon the selective removal of the chiral auxiliary under mild conditions. Moreover, the further hydrolysis of the alkoxydienyl moiety gave access to protected enantiopure β-keto amines 7.
Titolo: | Asymmetric Synthesis of Ethoxydienamines in Superbasic MediumMediated by Chiral Sulfinyl Group | |
Autori Riconosciuti: | ||
Autori: | Marco Blangetti; Gianluca Croce; Annamaria Deagostino; Eleonora Mussano; Cristina Prandi; Paolo Venturello | |
Data di pubblicazione: | 2011 | |
Abstract: | ABSTRACT: The direct addition of metalated alkoxydiene 2, obtained from R,β-unsaturated acetal 1 through a LIC-KORpromoted conjugated elimination reaction, to enantiopure sulfinimines 3 (both R and S N-sulfinyl imines) afforded Nsulfinyl alkoxydienyl amines 4 with high diastereoselectivity. Functionalized enantiopure alkoxydienyl amines 5 were then easily obtained upon the selective removal of the chiral auxiliary under mild conditions. Moreover, the further hydrolysis of the alkoxydienyl moiety gave access to protected enantiopure β-keto amines 7. | |
Volume: | 76 | |
Pagina iniziale: | 1814 | |
Pagina finale: | 1820 | |
Digital Object Identifier (DOI): | 10.1021/jo1024943 | |
URL: | http://pubs.acs.org/doi/abs/10.1021/jo1024943 | |
Rivista: | JOURNAL OF ORGANIC CHEMISTRY | |
Appare nelle tipologie: | 03A-Articolo su Rivista |
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