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.

Asymmetric Synthesis of Ethoxydienamines in Superbasic MediumMediated by Chiral Sulfinyl Group

BLANGETTI, Marco;DEAGOSTINO, Annamaria;PRANDI, Cristina;VENTURELLO, Paolo
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.
76
1814
1820
http://pubs.acs.org/doi/abs/10.1021/jo1024943
Marco Blangetti; Gianluca Croce; Annamaria Deagostino; Eleonora Mussano; Cristina Prandi; Paolo Venturello
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2318/83844
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