Asymmetric Synthesis of Ethoxydienamines in Superbasic MediumMediated by Chiral Sulfinyl Group

Blangetti, Marco; Gianluca, Croce; Deagostino, Annamaria; Eleonora, Mussano; Prandi, Cristina; Venturello, Paolo

doi:10.1021/jo1024943

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:	BLANGETTI, Marco Gianluca Croce DEAGOSTINO, Annamaria Eleonora Mussano PRANDI, Cristina VENTURELLO, Paolo mostra contributor esterni nascondi contributor esterni
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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http://hdl.handle.net/2318/83844

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