Lithiation of 2-unsubstituted Δ2-thiazolines and quenching with various electrophiles to 2-funcitonalized derivatives is reported. In particular quenching of thiazolines (1a and 1b) with trimethylsilyl chloride affords the corresponding 2-trimethylsilyl-Δ2-thiazolines (7a and 7b). The reactivity of these masked C2-anions toward electrophiles is described. Similar approach is developped for chiral 4-[(tert-butyldimethylsilyloxy)methyl]-2-thiazoline (12). The synthesis of the chiral 2-formyl derivative, generated in situ from the C2-anion and N-formylmorpholine, and its reactivity toward phosphonium salt are also discussed. © 1993.
Lithiation of delta2-thiazolines: the C2-anion approach to 2-substituted derivatives and their reactivity
FANTIN, Giancarlo;FOGAGNOLO, Marco;MEDICI, Alessandro;PEDRINI, Paola
1993
Abstract
Lithiation of 2-unsubstituted Δ2-thiazolines and quenching with various electrophiles to 2-funcitonalized derivatives is reported. In particular quenching of thiazolines (1a and 1b) with trimethylsilyl chloride affords the corresponding 2-trimethylsilyl-Δ2-thiazolines (7a and 7b). The reactivity of these masked C2-anions toward electrophiles is described. Similar approach is developped for chiral 4-[(tert-butyldimethylsilyloxy)methyl]-2-thiazoline (12). The synthesis of the chiral 2-formyl derivative, generated in situ from the C2-anion and N-formylmorpholine, and its reactivity toward phosphonium salt are also discussed. © 1993.File in questo prodotto:
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