Abstract
Several α-diazo β-keto nitriles bearing trans-2-allyl-, -vinyl-, or -phenylcycloalkyl groups were prepared and their intramolecular cyclopropanation reactions were examined. In the presence of Rh2(OAc)4 (1 mol%) as a catalyst, the allyl- and vinyl-substituted precursors were found to undergo cyclopropanation smoothly at ambient temperature to afford novel tricyclic α-keto cyclopropyl nitriles in 47–88% yields with diastereomeric ratios ranging from 79:21 to >99:1. On the other hand, the catalytic reactions of the phenyl-containing analogues did not give any cyclopropyl products, but instead provided functionalized hexahydrophenanthrene or tetrahydrocyclopentanaphthalene derivatives in quantitative yields.
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