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N‐Heterocyclic Carbene (NHC)‐Catalyzed/Lewis Acid Mediated Conjugate Umpolung of Alkynyl Aldehydes for the Synthesis of Butenolides: A Formal [3+2] Annulation
Author(s) -
Qi Jing,
Xie Xingang,
Han Runfeng,
Ma Donghui,
Yang Juan,
She Xuegong
Publication year - 2013
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.201204386
Subject(s) - synthon , umpolung , annulation , chemistry , lewis acids and bases , combinatorial chemistry , nucleophile , catalysis , carbene , electrophile , medicinal chemistry , organic chemistry
Reverse to success ! A new formal [3+2] annulation reaction combining alkynyl aldehydes and β,γ‐unsaturated α‐ketoesters has been disclosed by using a NHC‐catalyzed/Lewis acid mediated strategy. This cooperative catalysis strategy first allows the “allenolate” intermediate as a nucleophilic synthon at the β‐position to react with activated electrophilic reagents by an addition reaction as the key CC bond‐forming step.