Rearrangement of N-tert-Butanesulfinyl α-Halo Imines with Alkoxides to N-tert-Butanesulfinyl 2-Amino Acetals as Precursors of N-Protected and N-Unprotected α- …

…, S Mangelinckx, B Denolf, N De Kimpe

Index: Colpaert, Filip; Mangelinckx, Sven; Denolf, Bram; De Kimpe, Norbert Journal of Organic Chemistry, 2012 , vol. 77, # 14 p. 6023 - 6032

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Citation Number: 3

Abstract

Reaction of N-tert-butanesulfinyl α-halo imines with alkoxides afforded new N-tert- butanesulfinyl 2-amino acetals in good to excellent yield. These N-tert-butanesulfinyl 2- amino acetals are convenient precursors for the TMSOTf-promoted synthesis of the corresponding N-protected α-amino aldehydes and ketones, as well as for the HCl- promoted synthesis of 2-amino acetal hydrochlorides and α-amino ketone and α-amino ...