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2005
Cyclopentane derivatives
Q 0030
A Novel Synthesis, Including Asymmetric Synthesis, of 2,4,4-Trisubstituted
Based on the Reaction of 1-Chlorovinyl p-Tolyl Sulfoxides
23- 068 2-Cyclopentenones
with Acetonitrile and Its Homologues. — The present route to the title cyclopentenones is accomplished in three steps. The addition of cyanomethyllithium to 1-chlorovinyl sulfoxides is followed by treatment of the resulting diastereomeric adducts of type
(III) with LDA and than with lithium α-carbanions of various nitriles to give cyclic
enaminonitriles like compounds (V). Final acidic hydrolysis of the latter affords the
trisubstituted target compounds (to be continued). — (WAKASUGI, D.; SATOH*, T.;
Tetrahedron 61 (2005) 5, 1245-pp; Dep. Chem., Fac. Sci., Sci. Univ. Tokyo, Shinjuku,
Tokyo 162, Japan; Eng.) — Klein
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