Abstract
The coupling of ortho‐ and para‐phenols with secondary and tertiary boronic esters has been explored. In the case of para‐substituted phenols, after reaction of a dilithio phenolate species with a boronic ester, treatment with Ph3BiF2 or Martin's sulfurane gave the coupled product with complete enantiospecificity. The methodology was applied to the synthesis of the broad spectrum antibacterial natural product (−)‐4‐(1,5‐dimethylhex‐4‐enyl)‐2‐methyl phenol. For ortho‐substituted phenols, initial incorporation of a benzotriazole on the phenol oxygen atom was required. Subsequent ortho‐lithiation and borylation gave the coupled product, again with complete stereospecificity.
Highlights
The coupling of ortho- and para-phenols with secondary and tertiary boronic esters has been explored
We considered the counterintuitive use of the even more electron-rich para-phenolates for our coupling strategy (Scheme 1 c)
Chemie report our success in achieving this goal with two distinct methods for the stereospecific coupling of both ortho- and para-substituted phenols with secondary and tertiary boronic esters
Summary
The coupling of ortho- and para-phenols with secondary and tertiary boronic esters has been explored. Chemie report our success in achieving this goal with two distinct methods for the stereospecific coupling of both ortho- and para-substituted phenols with secondary and tertiary boronic esters.
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