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Ruthenium‐Catalyzed Cycloaddition of Nitrile Oxides and Alkynes: Practical Synthesis of Isoxazoles
Author(s) -
Grecian Scott,
Fokin Valery V.
Publication year - 2008
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.200801920
Subject(s) - nitrile , regioselectivity , ruthenium , cycloaddition , yield (engineering) , catalysis , chemistry , combinatorial chemistry , organic chemistry , medicinal chemistry , materials science , metallurgy
3,4‐Disubstituted and 3,4,5‐trisubstituted isoxazoles have been formed from alkynes and nitrile oxides in a ruthenium(II)‐catalyzed process (see scheme; cod=cycloocta‐l,5‐diene, Cp*=C 5 Me 5 ). These reactions are experimentally simple, proceed at room temperature, and produce isoxazoles with excellent regioselectivity in high yield.