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Synthesis of Highly Enantioenriched Bis‐spirooxindole Pyrrolizidine/Pyrrolidines through Asymmetric [3+2] Cycloaddition Reaction
Author(s) -
Shahrestani Naeimeh,
Tovfighmadar Kolsoum,
Eskandari Mehdi,
Jadidi Khosrow,
Notash Behrouz,
Mirzaei Peiman
Publication year - 2020
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202000056
Subject(s) - pyrrolizidine , chemistry , stereocenter , cycloaddition , isatin , pyrrolidine , diastereomer , enantioselective synthesis , 1,3 dipolar cycloaddition , mannich reaction , organic chemistry , combinatorial chemistry , stereochemistry , catalysis
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.