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Synfacts 2006(1): 0031-0031  
DOI: 10.1055/s-2005-921707
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Synthesis of Spiroisoxazolines

Contributor(s): Victor Snieckus, Farhad Nowrouzi
M. F. A. Adamo*, D. Donati, E. F. Duffy, P. Sarti-Fantoni
The Royal College of Surgeons in Ireland, Dublin, Ireland, and Università di Siena and Università di Firenze, Italy
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Publication History

Publication Date:
16 December 2005 (online)

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Significance

A three-component, one-pot procedure to assemble spiroisoxazolines from commercially available materials in satisfactory to high yields is reported. The final product is the result of a Knoevenagel and two Michael reactions sequence that perhaps is driven by the formation of a nitronate ammonium salt which leads to the final product after acidic workup. In the process, four stereogenic centers are formed with complete control of the relative stereochemistry giving the most thermodynamically stable diastereoisomer as a single isomer.