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Rhodium(II)‐ and Copper(II)‐Catalyzed Reactions of Enol Diazoacetates with Nitrones: Metal Carbene versus Lewis Acid Directed Pathways
Author(s) -
Qian Yu,
Xu Xinfang,
Wang Xiaochen,
Zavalij Peter J.,
Hu Wenhao,
Doyle Michael P.
Publication year - 2012
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/anie.201202525
Subject(s) - carbene , rhodium , enol , cycloaddition , chemistry , lewis acids and bases , copper , catalysis , metal , medicinal chemistry , combinatorial chemistry , organic chemistry , polymer chemistry
A complimentary cat. : Copper(II) hexafluoroantimonate catalyzes the formal [3+3] cycloaddition of Lewis acid activated nitrones and vinyl diazoacetates to produce 3,6‐dihydro‐1,2‐oxazines in yields of up to 96 % and diastereoselectivities greater than 25:1 (see scheme). This process compliments the metal carbene pathway that is catalyzed by rhodium(II) species.