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Silver-Assisted, Iridium-Catalyzed Allylation of Bis[(pinacolato)boryl]methane Allows the Synthesis of Enantioenriched Homoallylic Organoboronic Esters

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journal contribution
posted on 22.04.2016, 00:00 by Miao Zhan, Ren-Zhe Li, Ze-Dong Mou, Chao-Guo Cao, Jie Liu, Yuan-Wei Chen, Dawen Niu
Described here is an enantioselective approach of making chiral, β-substituted homoallylic organoboronic esters. In the presence of LiOtBu and a catalytic amount of silver salt, commercial bis­[(pinacolato)­boryl]­methane participated in the iridium-catalyzed asymmetric allylation reactions, delivered a “CH2B­(pin)” group, and yielded the title compounds from allylic carbonates. The synthetic utility of the prepared chiral organoboronates was demonstrated by their conversion to other important classes of compounds.