Chemistry–A European Journal

Reversal of regioselectivity and enhancement of rates of nitrile oxide cycloadditions through transient attachment of dipolarophiles to cyclodextrins

L Barr, SF Lincoln, CJ Easton

文献索引：Barr, Lorna; Lincoln, Stephen F.; Easton, Christopher J. Chemistry - A European Journal, 2006 , vol. 12, # 33 p. 8571 - 8580

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被引用次数: 15

摘要

Abstract The reactions of nitrile oxides with monosubstituted dipolarophiles, such as propiolamide, typically afford proportionally 80% or more of the 3, 5-disubstituted cycloadducts. By contrast, the reactions of 6 A-deoxy-6 A-propynamido-β-cyclodextrin with 4- tert-butylbenzonitrile oxide and 4-phenylbenzonitrile oxide afford> 90% and approximately 85% of the corresponding 3, 4-disubstituted isoxazoles, respectively. As well as reversing ...