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| - Stereoselective Synthesis of Both syn- and anti-N-tert-AlkylaminesUsing Highly Stereospecific Crotylation of Ketone-DerivedAcylhydrazones with Crotyltrichlorosilanes
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| - Crotyltrichlorosilanes reacted with ketone-derivedN-benzoylhydrazones in DMF without anycatalyst. This is the first example of highly stereospecific crotylation of ketimine analogues leadingto both syn- and anti-N‘-tert-alkyl-N-benzoylhydrazines. Different reactivities between (Z)- and (E)-crotylsilanes in terms of yields and selectivities were observed. A kinetic study with bothgeometrically pure (Z)- and (E)-crotylsilanes was performed. These reactions are most likely toproceed via a cyclic chairlike transition state where the aromatic group of hydrazones takes anaxial position. Both diastereomers of allylation products can be converted to the correspondingα,α-disubstituted homoallylic amines without epimerization.
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