Matthew SC, Glasspoole BW, Eisenberger P, Crudden CM * Queen’s University, Kingston,
Canada and Nagoya University, Japan
Synthesis of Enantiomerically Enriched Triarylmethanes by Enantiospecific Suzuki–Miyura
Cross-Coupling Reactions.
J. Am. Chem. Soc. 2014;
136: 5828-5831
Key words
Suzuki reaction - triarylmethanes - enantiospecificity
Significance
Recently, enantioselective cross-couplings have received increased attention due to
their potential for easily constructing valuable chiral molecules. However, when compared
to non-enantioselective variants, there are only a limited number of reports which
describe desirable levels of selectivities. The group of Crudden reports a novel route
towards valuable chiral triarylmethanes via a stereospecific Suzuki cross-coupling.
Comment
The authors utilize chiral dibenzylic boronic esters (synthesis described) and aryl
iodides to stereospecifically access chiral triarylmethanes using the inexpensive
palladium pre-catalyst Pd(PPh3)4. A range of chiral boronic esters are synthesized from the benzyl carbamates with
good to excellent enantiomeric ratios, which are easily converted into the target
products with up to 100% stereospecificity.
