Aryl nitrile oxide cycloaddition reactions in the presence of pinacol boronic acid ester

Beilstein Journal of Organic Chemistry

Sebastian M. Marcuccio¹  Sarah L. Harding²  G. Paul Savage² 

[1] Advanced Molecular Technologies Pty Ltd, Unit 1, 7–11 Rocco Drive, Scoresby, VIC 3179, Australia;CSIRO Materials Science and Engineering, Private Bag 10, Clayton South MDC, Vic 3169, Australia;

关键词: dipolar cycloaddition;    heterocycle;    nitrile oxide;    hypervalent iodine oxidation;    pinacol boronic acid esters;   

DOI  :  10.3762/bjoc.8.67

来源: DOAJ

【 摘 要 】

An aryl substrate with dual functionality consisting of a nitrile oxide and a pinacolyl boronate ester was prepared by mild hypervalent iodine oxidation (diacetoxyiodobenzene) of the corresponding aldoxime, without decomposition of the boronate functionality. The nitrile oxide was trapped in situ with a variety of dipolarophiles to yield aryl isoxazolines with the boronate ester function intact and available for subsequent reaction.

【 授权许可】

Unknown