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"Design" of boron-based compounds as pro-nucleophiles and co-catalysts for indium(I)-catalyzed allyl transfer to various Csp3-type electrophiles.

We have recently uncovered a general indium(I)-catalyzed method for allylations and propargylation of acetals and ketals with a water- and air-stable allyl boronate. By using a more reactive allyl borane, we have successfully extended this methodology to the more challenging C-C coupling with ethers. Herein, we report an improved methodology for the indium(I)-catalyzed allylation of acetals and ethers, through combination of the allyl boronate with a commercially available "hard" Lewis acid, B-methoxy-9-BBN (BBN=borabicyclo[3.3.1]nonane), as an effective co-catalyst. Significantly, our work highlights for the first time the correlation between the Lewis acidity of "electrophilic" boron-based compounds and their "nucleophilic" reactivity in Csp(3)-Csp(3) couplings, catalyzed by a "soft" low-oxidation main group metal. In addition, we also report several applications of these methodologies to the selective synthesis of various carbohydrate derivatives.