Abstract
Stereogenic main group elements are clearly generating interest in the enantioselective catalysis field. Surprisingly, while chiral organoboron reagents are very useful in stereoselective transformations, few scaffolds stereogenic at boron and configurationally stable have been reported to date. Herein, we describe an original library of chiral NHC-boranes, stereogenic at the boron atom, that has been prepared in only a few steps and in good yields (up to 93%). Key steps involve a chlorination/arylation sequence in the presence of simple Grignard reagents from bicyclic NHC-boranes. The high and unprecedented diastereoselectivity observed during the second step (up to 99 : 1 dr) has been rationalized through a plausible SRN1 mechanism thanks to EPR observations and DFT calculations.
Highlights
When it comes to enantioselective catalysis, the literature on the subject is widely dominated by transition metal catalysts
While chiral organoboron reagents are very useful in stereoselective transformations, few scaffolds stereogenic at boron and configurationally stable have been reported to date
The high and unprecedented diastereoselectivity observed during the second step has been rationalized through a plausible SRN1 mechanism thanks to EPR observations and DFT calculations
Summary
When it comes to enantioselective catalysis, the literature on the subject is widely dominated by transition metal catalysts.
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