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Methods of Cleavage of 2-Isoxazolines

[ Vol. 8 , Issue. 5 ]

Author(s):

Jaipal R. Nagireddy, Mohammed-Abdul Raheem, Jamie Haner and William Tam   Pages 659 - 700 ( 42 )

Abstract:


This review details the numerous methods of cleavage of 2-isoxazolines and the application of these methods in the synthesis of natural products. 2-Isoxazolines can be cleaved to provide a vast array of functionalities depending on the cleavage conditions used and nature of the substrate. Several cleavage reactions of 2-isoxazolines are covered, including, reductive cleavage by hydrogenolysis using various metal catalysts and under various conditions; oxidative cleavage using ozonolysis, Br2 and ethylene glycol, and peracids; cleavage using Mo(CO)6 or Mo(CO)3(MeCN)3, thermolysis, photolysis, flash vacuum thermolysis, I2, DBU, sodium alkoxides, Et3N, EtMgBr, and mineral acids.

Keywords:

2-isoxazoline, heterocycles, ring cleavage, beta-hydroxy ketones, 1,3-dipolar cycloaddition, REDUCTIVE CLEAVAGE, Electrochemical Cleavage, Lithium Aluminum Hydride

Affiliation:

Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph,Guelph, Ontario, N1G 2W1, Canada.



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