Department of Chemistry, University of Nebraska-Lincoln, Lincoln, NE 68588-0304, USA.
Chem Commun (Camb). 2018 May 8;54(38):4838-4841. doi: 10.1039/c8cc01563e.
γ,δ-Unsaturated amides in which the alkene moiety bears an aryl or heteroaryl substituent undergo regioselective rhodium-catalyzed δ-borylation by pinacolborane to afford chiral secondary benzylic boronic esters. The results contrast the γ-borylation of γ,δ-unsaturated amides in which the disubstituted alkene moiety bears only alkyl substituents; the reversal in regiochemistry is coupled with a reversal in the sense of π-facial selectivity.
其中烯基部分带有芳基或杂芳基取代基的γ,δ-不饱和酰胺经频哪醇硼烷进行区域选择性铑催化δ-硼化反应，生成手性仲苄基硼酸酯。结果与γ,δ-不饱和酰胺的γ-硼化反应形成对比，其中二取代烯基部分仅带有烷基取代基；区域化学的反转与π-面选择性的反转相关联。
