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Highly Regioselective Allylic Alkylation of Dienyl Acetates and Enynyl Acetates Catalyzed by an Iridium Complex
Author(s) -
Takeuchi Ryo,
Tanabe Keisuke
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20000602)39:11<1975::aid-anie1975>3.0.co;2-i
Subject(s) - regioselectivity , allylic rearrangement , iridium , tsuji–trost reaction , nucleophile , chemistry , catalysis , alkylation , medicinal chemistry , diene , selectivity , organic chemistry , natural rubber
An efficient catalyst for allylic alkylation of dienyl and enynyl acetates, [{Ir(cod)Cl} 2 ] (cod=cycloocta‐1,5‐diene) catalyzes the regioselective nucleophilic attack at the substituted allylic terminus to give a branched product in high selectivity. These results suggest the intermediacy of a 1‐(1‐alkenyl)‐ and 1‐(1‐alkynyl)π‐allyliridium species, respectively (see scheme).