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Highly Selective Allylic Alkylation with a Carbon Nucleophile at the More Substituted Allylic Terminus Catalyzed by an Iridium Complex: An Efficient Method for Constructing Quaternary Carbon Centers
Author(s) -
Takeuchi Ryo,
Kashio Mikihiro
Publication year - 1997
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199702631
Subject(s) - nucleophile , allylic rearrangement , iridium , tsuji–trost reaction , catalysis , alkylation , carbon fibers , quaternary carbon , chemistry , combinatorial chemistry , organic chemistry , enantioselective synthesis , computer science , algorithm , composite number
The selective construction of quaternary carbon centers , which are frequently found in natural products, is essential to many syntheses. A new method relying on the iridium complex [Ir(cod)Cl] 2 as the catalyst can be used for the allylic alkylation of acyclic compounds 1 [Eq (a)]. The products are obtained in yields between 70 and 85% and with a selectivity of 100%. cod = cyclooctadiene.