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Synlett 1993; 1993(4): 256-258
DOI: 10.1055/s-1993-22422
DOI: 10.1055/s-1993-22422
letter
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Selective Conjugate Addition of Benzylamine to 2-Thiazolyl α,β-Enone Derived from D-Glyceraldehyde Acetonide. An Exploratory Study Toward the Synthesis of Aminated Ulosonic Acids
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Publication History
Publication Date:
19 March 2002 (online)
The addition of benzylamine to a thiazole bearing α,β-unsaturated ketone derived from D-glyceraldehyde acetonide in methylene dichloride at -70 °C leads to the (R)-β-amino ketone (syn adduct ) with good level of stereoselectivity (ds 90%); this kinetic product is prevented to equilibrate to the (S)-epimer (anti-adduct) by in situ ketalization to pyranose which serves as an intermediate to a 4-amino-3,4-dideoxy-D-threo-hexulosonic acid derivative.