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

Title
Copper-Catalyzed Enantiotopic-Group-Selective Allylation of gem-Diborylalkanes
Authors
김민재SHIN, MINKYEONGKIM, JUNGHOONCHO, SEUNG HWAN
Date Issued
Jan-2021
Publisher
American Chemical Society
Abstract
We report a copper-catalyzed enatiotopic-group-selective allylation of gem-diborylalkanes with allyl bromides. The combination of copper(I) bromide and H8–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 transmetalation of gem-diborylalkanes with chiral copper complex occurs to generate chiral α-borylalkyl-copper species for the first time. Additional synthetic applications to the synthesis of various chiral building blocks are also included.
URI
http://oasis.postech.ac.kr/handle/2014.oak/104912
ISSN
0002-7863
Article Type
Article
Citation
Journal of the American Chemical Society, vol. 143, page. 1069 - 1077, 2021-01
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