An efficient synthesis of oxetanones from α,β-epoxy diazomethyl ketones.

Add time:08/26/2019    Source:sciencedirect.com

Treatment of α,β-epoxy diazomethyl ketones 1a–h with SnCl4 in dichloromethane at −78°C leads to β-chloro-α-hydroxy diazoketones 3a–h in good yields. The opening of the epoxide ring takes place in a syn manner with retention of configuration at Cβ. The chloro hydroxy diazoketones 3 are converted into the oxetanones 4a–h on treatment with BF3-OEt2. For epoxy diazomethyl ketones 1b,i-1 the intermediate chlorohydrins 3 could not be isolated, however the corresponding oxetanones were obtained in acceptable yields.Selective opening of the epoxide ring of 1 leads to β-chloro-α-hydroxy diazoketones 3. With BF3·OEt2 compounds 3 can be readily transformed to the oxetanones 4.

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