Asymmetric synthesis of ethoxydienamines in superbasic medium mediated by chiral sulfinyl group |
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Authors: | Blangetti Marco Croce Gianluca Deagostino Annamaria Mussano Eleonora Prandi Cristina Venturello Paolo |
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Affiliation: | Dipartimento di Chimica Generale e Chimica Organica, Università degli Studi di Torino, Via P. Giuria, 7-10125 Torino, Italy. |
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Abstract: | The direct addition of metalated alkoxydiene 2, obtained from α,β-unsaturated acetal 1 through a LIC-KOR-promoted conjugated elimination reaction, to enantiopure sulfinimines 3 (both R and SN-sulfinyl imines) afforded N-sulfinyl 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. |
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