Methods of Cleavage of 2-Isoxazolines

Author(s): Jaipal R. Nagireddy, Mohammed-Abdul Raheem, Jamie Haner, William Tam.

Journal Name: Current Organic Synthesis

Volume 8 , Issue 5 , 2011

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

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Article Details

VOLUME: 8
ISSUE: 5
Year: 2011
Page: [659 - 700]
Pages: 42
DOI: 10.2174/157017911796957348
Price: $58

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