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N-heterocyclic carbene catalysed homoenolate addition to 3-methyl-4-nitro-5-styrylisoxazoles
Authors:Diana Salazar Illera  Surisetti Suresh  Maria Moccia  Gea Bellini  Michele Saviano  Mauro F.A. Adamo
Affiliation:1. Centre for Synthesis and Chemical Biology (CSCB), Department of Pharmaceutical and Medicinal Chemistry, The Royal College of Surgeons in Ireland, 123 St. Stephen’s Green, Dublin 2, Dublin, Ireland;2. Centro Nazionale delle Ricerche, Istituto di Cristallografia, via Amendola 122/o, 70126 Bari, Italy
Abstract: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.
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