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Enantioselective Organocatalyzed Michael Additions of Nitroalkanes to 4‐Arylidenedihydrofuran‐2,3‐diones and 4‐Arylidenepyrrolidine‐2,3‐diones
Author(s) -
Fofana Mouhamadou,
Dudog Yohan,
Bertrand Laura,
Constantieux Thierry,
Rodriguez Jean,
Ndiaye Ibrahima,
Bonne Damien,
Bugaut Xavier
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000460
Subject(s) - enantioselective synthesis , electrophile , organocatalysis , chemistry , michael reaction , catalysis , organic chemistry , hydrogen bond , combinatorial chemistry , molecule
Tremendous efforts have been devoted to the development of organocatalytic enantioselective Michael additions of nitroalkanes to α,β‐unsaturated carbonyl compounds. However, using highly substituted electrophiles remain challenging, since the additional substituents decrease the electrophilicity. β‐Arylidene‐α‐ketolactones and α‐ketolactams are used as highly electrophilic Michael acceptors that afford the corresponding products in moderate to good yields, with high enantioselectivities. This success relies on their rigid structure that prevents deconjugation and the efficient recognition of the α‐dicarbonyl motif by the hydrogen‐bond donor catalyst.