Spirocyclic compoundsR 0015 DOI: 10.1002/chin.201213116

Synthesis of Diverse Spiroisoxazolidinohydantoins by Totally Regio- and Dia-stereoselective 1,3-Dipolar Cycloadditions. — Title compounds are produced from 5-carboxymethylene hydantoins generated by reaction of carbodiimides and acetylene-dicarboxylic acid monoesters under mild conditions. Products are mostly obtained as E-isomers whereby, in some cases mixtures of E- and Z-isomers or sole Z-isomers [cf. (XVIII)] are isolated. Subsequent 1,3-dipolar cycloaddition reaction with either acyclic or cyclic nitrones results in the formation of desired title compounds with total control of the regio- and diastereoselectivity. Using an enantiomerically pure chiral pyrroline nitrone, the reaction leads to an optically active product (no yield given). — (BELLUCCI, M. C.; MARCELLI, T.; SCAGLIONI, L.; VOLONTERIO*, A.; RSC Adv. 1 (2011) 7, 1250-1264, http://dx.doi.org/10.1039/c1ra00573a ; Dep. Chem., Mater. Chem. Eng., Politec. Milano, I-20131 Milano, Italy; Eng.) — S. Adam

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ChemInform 2012, 43, issue 13 © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

ChemInform 2012, 43, issue 13 © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim