Copper-Catalyzed Enantiotopic-Group-Selective Allylation of gem-Diborylalkanes.
J Am Chem Soc
; 143(2): 1069-1077, 2021 01 20.
Article
en En
| MEDLINE
| ID: mdl-33393768
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.
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01-internacional
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MEDLINE
Idioma:
En
Revista:
J Am Chem Soc
Año:
2021
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Article