N-heterocyclic carbene catalysed homoenolate addition to 3-methyl-4-nitro-5-styrylisoxazoles

We describe the development of an N-heterocyclic carbene catalysed homoenolate addition to 4-nitro-5-styrylisoxazoles to give substituted cyclopentanones with a unique substitution pattern and as single diastereoisomers. The synthetic utility of the cyclopentanones obtained was briefly explored through their conversion into α-fluorinated diketones and keto acids.