Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 9, Pages 4631-4639Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00227
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- Italian Ministero dell'Universita e della Ricerca (MIUR) [PRIN 20109Z2XRJ_003, 20109Z2XRJ_006]
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A green and efficient 1,3-dipolar cycloaddition of nitrones with different styrenes and cinnamates using a catalytic amount of gamma-cyclodextrin (gamma-CD) in water has been developed to give substituted isoxazolidines. gamma-CD was found to be highly efficacious in carrying out this reaction under an eco-friendly environment, affording moderate to excellent yields and, in some cases, excellent diastereomeric excess (up to > 95%) at 100 degrees C in 8-12 h. The catalyst can be easily recuperated and recycled for several times without loss of activity. Water, an eco-friendly reaction medium, has been utilized for the first time, to the best of our knowledge, in this reaction. The credit of the presented protocol includes high yields and catalyst reusability, and precludes the use of organic solvents. The use of in silico calculations allowed us to rationalize the obtained results, and to improve the stereoselectivity.
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