Enantioconvergent Hydroboration of E/Z-Mixed Trisubstituted Alkenes.
J Am Chem Soc
; 146(30): 21089-21098, 2024 Jul 31.
Article
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| MEDLINE
| ID: mdl-38994866
ABSTRACT
The lack of mode for chirality recognition makes it particularly challenging to carry out asymmetric transformations on E/Z-mixed minimally functionalized trisubstituted alkenes. Here, we report a catalytic enantioconvergent hydroboration of minimally functionalized trisubstituted E/Z-mixed alkenes to construct chiral organoboronic esters with excellent enantioselectivity using chiral radical cobalt catalyst. This C(sp3)-H borylation protocol showed good functional group tolerance and products could be converted to valuable compounds via C-B derivatizations. The mechanistic studies, which included control experiments, nonlinear effect experiments, deuterated labeling experiments, and X-ray diffraction, demonstrated that the favorable compatibility between the thermodynamically unfavorable isomerization and hydroboration was the key factor in achieving convergent transformation.
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Bases de dados:
MEDLINE
Idioma:
En
Revista:
J Am Chem Soc
Ano de publicação:
2024
Tipo de documento:
Article