Direct Conversion of Nitroalkenes to Carbonyl Compounds

The direct conversion of nitroalkenes into ketones is especially useful for the preparation of arylacetones. They are readily prepared by the condensation of aromatic aldehydes with nitroethane and by the subsequent Nef reaction 42 Typical examples are presented in Eq. 6.2237 and Eq. 6.23 the product of Eq. 6.23 is used for total synthesis of perylenequinone, calphostin D, which is a potent inhibitor of protein kinase C.42b 

Iodotrimethylsilane generated in situ from chlorotrimetylsilane and sodium iodide effects the reduction of nitroalkenes into ketones at 0 °C. This method is useful for the conversion of nitro steroids or nitro terpenoids to the corresponding ketones (Eq. 6.24).43 

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