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

Described here is an enantioselective approach of making chiral, β-substituted homoallylic organoboronic esters. In the presence of LiO t Bu and a catalytic amount of silver salt, commercial bis­[(pinacolato)­boryl]­methane participated in the iridium-catalyzed asymmetric allylation reactions, deliv...

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Published inACS catalysis Vol. 6; no. 5; pp. 3381 - 3386
Main Authors Zhan, Miao, Li, Ren-Zhe, Mou, Ze-Dong, Cao, Chao-Guo, Liu, Jie, Chen, Yuan-Wei, Niu, Dawen
Format Journal Article
LanguageEnglish
Published American Chemical Society 06.05.2016
Subjects
iridium
bis[(pinacolato)boryl]methane
enantioselective allylation
catalysis
silver
boronic esters
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Summary:Described here is an enantioselective approach of making chiral, β-substituted homoallylic organoboronic esters. In the presence of LiO t Bu 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.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.6b00719