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Chemoselective, Regioselective, and Enantioselective Allylations of NH2OH under Iridium Catalysis

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journal contribution
posted on 21.05.2019, 13:36 by Jiteng Chen, Qingchun Liang, Xiaoming Zhao
The utilization of unprotected NH2OH, which is not only an oxygen nucleophile but also a nitrogen nucleophile, in iridium-catalyzed allylic substitution is realized under mild conditions. The chemoselectivity, stereoselectivity, and multiple allylation are controlled by adjusting the reaction conditions. This method produces the N-(1-allyl)­hydroxylamines in good to high yields with high level of chemoselectivities, regioselectivities, and enantioselectivities. The application of allylated hydroxylamine (R)-3a in the synthesis of diallylated hydroxylamine 6 is achieved, along with an excellent diastereomeric ratio.