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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-amino Carbonyl Compounds

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-amino Carbonyl Compounds

Filip Colpaert, Sven Mangelinckx, Bram Denolf, Norbert De Kimpe

J Org Chem. 2012 Jul 20;77(14):6023-32.

PMID: 22747442

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 aldehyde hydrochlorides in high yield. Via this method, an asymmetric synthesis of (S)-cathinone hydrochloride (er 94:6) was achieved.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP16735196	Cathinone hydrochloride		16735-19-6	Price

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