Chemistry of aminoketene dithioacetals: preparation of protected α-amino aldehydes and ketones and formation of nitrogen heterocycles
- 1 January 1987
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 10,p. 775-776
- https://doi.org/10.1039/c39870000775
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.Keywords
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