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Copper-Catalyzed Enantiotopic-Group-Selective Allylation of gem-Diborylalkanes

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Title
Copper-Catalyzed Enantiotopic-Group-Selective Allylation of gem-Diborylalkanes
Author(s)
Kim, Minjae; Bohyun Park; Shin, Minkyeong; Suyeon Kim; Kim, Junghoon; Mu-Hyun Baik; Cho, Seung Hwan
Publication Date
2021-01
Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.143, no.2, pp.1069 - 1077
Publisher
AMER CHEMICAL SOC
Abstract
We report a copper-catalyzed enatiotopic-group-selective allylation of gem-diborylalkanes with allyl bromides. The combination of copper(I) bromide and H-8-BINOL derived phosphoramidite ligand proved to be the most effective catalytic system to provide various enantioenriched homoallylic boronate esters, containing a boron-substituted stereogenic center that is solely derived from gem-diborylalkanes, in good yields with high enantiomeric ratios under mild conditions. Experimental and theoretical studies have been conducted to elucidate the reaction mechanism, revealing how the enatiotopic-group-selective trans-metalation of gem-diborylalkanes with chiral copper complex occurs to generate chiral alpha-borylalkyl-copper species for the first time. Additional synthetic applications to the synthesis of various chiral building blocks are also included.
URI
https://pr.ibs.re.kr/handle/8788114/9200
DOI
10.1021/jacs.0c11750
ISSN
0002-7863
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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