Copper-Catalyzed Enantiotopic-Group-Selective Allylation of gem-Diborylalkanes
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- Title
- Copper-Catalyzed Enantiotopic-Group-Selective Allylation of gem-Diborylalkanes
- Authors
- 김민재; SHIN, MINKYEONG; KIM, JUNGHOON; CHO, SEUNG HWAN
- Date Issued
- 2021-01
- 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://oasis.postech.ac.kr/handle/2014.oak/104912
- DOI
- 10.1021/jacs.0c11750
- ISSN
- 0002-7863
- Article Type
- Article
- Citation
- JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 143, no. 2, page. 1069 - 1077, 2021-01
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