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.
Selective Conjugate Addition of Benzylamine to 2-Thiazolyl α,β-Enone Derived from D-Glyceraldehyde AcetonideAn Exploratory Study Toward the Synthesis of Aminated Ulosonic Acids
DONDONI, Alessandro;MARRA, Alberto
1993
Abstract
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.File in questo prodotto:
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