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Synfacts 2024; 20(06): 0593
DOI: 10.1055/s-0043-1773243
DOI: 10.1055/s-0043-1773243
Metals in Synthesis
Enantioselective Synthesis of Organoborons Enabled by Cyclopropene Ring Opening
Huang M.-Y,
Zhao J.-B,
Zhang C.-D,
Zhou Y.-J,
Lu Z.-S,
Zhu S.-F.
*
Nankai University, Tianjin, P. R. of China
Enantioselective α‑Boryl Carbene Transformations.
J. Am. Chem. Soc. 2024;
146: 9871-9879
DOI: 10.1021/jacs.3c14766.
Enantioselective α‑Boryl Carbene Transformations.
J. Am. Chem. Soc. 2024;
146: 9871-9879
DOI: 10.1021/jacs.3c14766.
Significance
Zhu and coworkers report an enantioselective synthesis of organoboron compounds via the α-boryl carbene. This work expands on the scarcely used α-boryl carbene intermediate in a wide range of applications.
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Comment
While investigating the mechanism, KIE studies revealed that the rate-determining step was likely the cyclopropene ring opening. Interestingly, it is suggested that the α-boryl carbene is likely a donor-type carbene when compared to the known α-ester and hydrogen carbenes.
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Publication History
Article published online:
14 May 2024
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