期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 67, 期 15, 页码 5359-5364出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo0258599
关键词
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Crotyltrichlorosilanes reacted with ketone-derived N-benzoylhydrazones in DMF without any catalyst. This is the first example of highly stereospecific crotylation of ketimine analogues leading to 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 both geometrically pure (Z)- and (E)-crotylsilanes was performed. These reactions are most likely to proceed via a cyclic chairlike transition state where the aromatic group of hydrazones takes an axial position. Both diastereomers of allylation products can be converted to the corresponding alpha,alpha-disubstituted homoallylic amines without epimerization.
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