Asymmetric synthesis of diverse boronic acids has remained an important challenge. We developed an organocatalytic method for synthesis of various α-trifluoromethyl boronic acids by reaction of α-trifluoromethyl diazomethane and organoboronates in the presence of BINOL catalysts. The reaction proceeds with high levels of selectivity affording α-trifluoromethyl boronates. In situ allylboration and oxidation can afford various chiral alcohols. Purification of the α-trifluoromethyl boronic acids and conversion to boroxine allows it to react with ketones, indole and amino acid to afford the desired product with retention of the configuration. This method can be expanded in the same way using trimethylsilyl diazo compound. A new version of the reaction suitable for synthesis of chiral trifluoromethyl allenols will also be presented.

Synthesis of chiral α-trifluoromethyl boronic acids by catalytic homologation

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