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Direct Asymmetric Aza‐Vinylogous‐Type Michael Additions of Nitrones from Isatins to Nitroalkenes
Author(s) -
Zhan Gu,
Shi MingLin,
Lin WeiJia,
Ouyang Qin,
Du Wei,
Chen YingChun
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201701290
Subject(s) - nitrone , moiety , chemistry , bifunctional , electrophile , combinatorial chemistry , pyrrolizidine , thiourea , stereoselectivity , michael reaction , amine gas treating , nitrosobenzene , organic chemistry , stereochemistry , cycloaddition , catalysis
Nitrones commonly act as 1,3‐dipoles and electrophiles to furnish valuable isoxazolidine and N ‐hydroxyl products, respectively. They also can be converted to nitrone ylide species and undergo [3+2] formal cycloadditions to access N ‐hydroxyl pyrrolidines. Here, asymmetric direct aza‐vinylogous‐type additions of nitrones from isatins to nitroalkenes are presented, catalyzed by a bifunctional thiourea‐tertiary amine, affording highly functionalized nitrones with extended carbon skeletons in excellent stereoselectivity. Notably, the nitrone moiety can be easily removed, thus furnishing the formal asymmetric α‐functionalization of alkylamine‐type substances. Moreover, the remaining electrophilic nitrone motif enables the subsequent annulations to construct spirocyclic products in high molecular complexity and diversity, which might have potential applications for drug discovery.