Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 6, Issue 9, Pages 2522-2529Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201100096
Keywords
allylation; boron; carbohydrates; C-C coupling; indium
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Funding
- Japan Society for the Promotion of Science (JSPS)
- University of Tokyo, MEXT, Japan
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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.
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