Syntheses of Three- and Five-Membered Carbocycles via Diene-Titanium Complexes

doi:10.1055/s-2008-1072530

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Synfacts 2008(5): 0525-0525
DOI: 10.1055/s-2008-1072530

Metal-Mediated Synthesis

Syntheses of Three- and Five-Membered Carbocycles via Diene-Titanium Complexes

Contributor(s): Paul Knochel, Tobias Thaler
P. Bertus*, C. Menant, C. Tanguy, J. Szymoniak*
Université de Reims Champagne-Ardenne, France

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Publikationsdatum:
23. April 2008 (online)

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Significance

The substrate-dependent 1,2- or 1,4-dicarbanion reactivity of diene-titanium complexes, which are generated from homoallylic Grignard reagents and Ti(Oi-Pr)₄ via a Kulinkovich-type pathway, is demonstrated in this article. Thus, 3-cyclopentenylamines can be selectively accessed from nitriles and spiro-vinylcyclopropane lactams/carbamates from cyanoesters and -carbonates.