Issue 10, 1987
From the journal:

Journal of the Chemical Society, Chemical Communications

Chemistry of aminoketene dithioacetals: preparation of protected α-amino aldehydes and ketones and formation of nitrogen heterocycles

Philip C. Bulman Page,   Monique B. van Niel  and  Donald Westwood  

Abstract

The ambident anion (2) derived from primary aminoketene dithioacetal (1, R = Ph) reacts with alkyl halides at the carbon atom to give remarkably stable primary imines which may be reduced to give protected α-amino ketones using borane in quantitative yield, and under similar conditions aminoketene dithioacetal (1, R = Ph) gives the protected α-amino aldehyde (15); anion (2) reacts with the bis-electrophile epichlorohydrin to give the nitrogen heterocycle (9) in 80% yield, and other related chemistry is also reported.

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Article information

DOI
https://doi.org/10.1039/C39870000775
Article type
Paper

J. Chem. Soc., Chem. Commun., 1987, 775-776

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Chemistry of aminoketene dithioacetals: preparation of protected α-amino aldehydes and ketones and formation of nitrogen heterocycles

P. C. B. Page, M. B. van Niel and D. Westwood, J. Chem. Soc., Chem. Commun., 1987, 775 DOI: 10.1039/C39870000775

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