3 years ago

Synthesis of Highly Enantioenriched Bis‐spirooxindole Pyrrolizidine/Pyrrolidines via Asymmetric [3+2] Cycloaddition Reaction

Synthesis of Highly Enantioenriched Bis‐spirooxindole Pyrrolizidine/Pyrrolidines via Asymmetric [3+2] Cycloaddition Reaction
Naeimeh Shahrestani, Kolsoum Tovfighmadar, Mehdi Eskandari, Khosrow Jadidi, Behrouz Notash, Peiman Mirzaei

Synthesis of highly enantioenriched bis‐spirooxindole pyrrolizidine scaffold was established using 1,3‐dipolar cycloaddition of isatin‐derived azomethine ylides by (E)‐2‐oxoindolin‐3‐ylidene acetyl sultam with four contiguous and two quaternary stereogenic centers in generally high yields (up to 96%) and diastereoselectivities (up to 99 : 1). In addition, highly enantioenriched bis‐spirooxindole pyrrolidines were generated in high yields and highly regio‐ and ‐diastereoselectivities (up to 99 : 1) by utilizing this chiral auxiliary controlled method. The obtained cycloadducts underwent retro‐Mannich ring‐opening cyclization and produced new diastereoisomers of bis‐spirooxindole pyrrolizidine/pyrrolidines skeleton that could not be accessed by direct 1,3‐dipolar cycloaddition.

Publisher URL: https://onlinelibrary.wiley.com/doi/abs/10.1002/ajoc.202000056

DOI: 10.1002/ajoc.202000056

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