An experimental and theoretical study on the remarkable influence of protecting groups on the selectivity of addition of amines to vinyl sulfone-modified hex-2-enopyranosides.

@article{Bhattacharya2010AnEA,
  title={An experimental and theoretical study on the remarkable influence of protecting groups on the selectivity of addition of amines to vinyl sulfone-modified hex-2-enopyranosides.},
  author={Rahul Bhattacharya and Manoj K. Kesharwani and Chinmoy Manna and Bishwajit Ganguly and Cheravakattu Gopalan Suresh and Tanmaya Pathak},
  journal={The Journal of organic chemistry},
  year={2010},
  volume={75 2},
  pages={
          303-14
        }
}
Although phenylmethylene-protected vinyl sulfone-modified carbohydrate 2alpha reacts with both primary and secondary amines in Michael fashion to afford aminated products, only primary amines react with the dibenzyl-protected 3alpha, 6-O-trityl-protected 4alpha, and unprotected 5alpha, highlighting for the first time the remarkable influence of protecting groups on the reaction patterns of vinyl sulfone-modified carbohydrates. The quantum chemical calculations suggest that the Michael addition… CONTINUE READING
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