2014ChemistryOpenOpen access

Highly Efficient and Stereoselective Construction of Bispirooxindole Derivatives via a Three‐Component 1,3‐Dipolar Cycloaddition Reaction

Qin Xu, De Wang, Yin Wei, Min Shi

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Abstract

A highly regio- and stereoselective synthesis of bispirooxindoles by 1,3-dipolar cycloaddition of in situ generated azomethine ylides from isatin and proline to different electron-deficient alkenes has been developed. The synthesis affords the desired bispiro scaffold compounds in excellent yields with high regioselectivity under mild conditions. The stereochemistry was determined by single-crystal X-ray analysis.

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A highly regio- and stereoselective synthesis of bispirooxindoles by 1,3-dipolar cycloaddition of in situ generated azomethine ylides from isatin and proline to different electron-deficient alkenes has been developed. The synthesis affords the desired bispiro scaffold compounds in excellent yields with high regioselectivity under mild conditions. The stereochemistry was determined by single-crystal X-ray analysis.

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Available abstract

A highly regio- and stereoselective synthesis of bispirooxindoles by 1,3-dipolar cycloaddition of in situ generated azomethine ylides from isatin and proline to different electron-deficient alkenes has been developed. The synthesis affords the desired bispiro scaffold compounds in excellent yields with high regioselectivity under mild conditions. The stereochemistry was determined by single-crystal X-ray analysis.

Key concepts: Regioselectivity, Stereoselectivity, Cycloaddition, 1,3-Dipolar cycloaddition, Isatin, Chemistry, Combinatorial chemistry, Proline

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