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2005
C-C bond formation
O 0282
Solvent-Dependent Chemoselectivities in Additions of β-Carbonyl Imines to
with CTAN. — The outcome of the Ce(IV)-mediated oxidative
04- 050 Allyltrimethylsilane
addition of allylsilane (II) to imines (I) is remarkably influenced by the choice of solvent. In methylene chloride, dihydropyrrole products are obtained exclusively, whereas
in MeCN allylation products are formed. In every case, the addition of excess Et3N to
the crude reaction mixtures avoids hydrolysis of the products initiated by the Ce(III)
product ion. The use of excess Ce(IV)-salt only slightly enhances the yields and produces some diallylated products. — (ZHANG, Y.; RAINES, A. J.; FLOWERS*, R. A.
I.; J. Org. Chem. 69 (2004) 19, 6267-6272; Dep. Chem., Lehigh Univ., Bethlehem, PA
18015, USA; Eng.) — Klein
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