D. Ghosh, S. Saravanan, N. Gupta
Nov 1, 2014
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Influential Citations
6
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Journal
Asian Journal of Organic Chemistry
Abstract
The present work demon- strates the use of phosphotungstic acid (H3PW12O40·H2O) as an efficient catalyst for the allylation of isatin de- rivatives as well as N-tert-butyloxycar- bonyl (Boc)-a-amido sulfones with al- lyltributyltin as an allylating agent under solvent-free conditions at room temperature. Excellent allylation product yields of up to 99 % for the isatins substrates and good to excel- lent yields of up to 98 % for the N- Boc a-amido sulfones were obtained. The present allylation protocol is scal- able as demonstrated by allylation of N-methylisatin at 1 g scale. Based on 1 H, 13 C, and 31 P NMR studies a catalyt- ic cycle was proposed for allylation of isatins as well as N-Boc amido sul- fones. The allylation products N-Boc homoallyl amines were successfully epoxidized to get multifunctional compounds, which are valuable inter- mediates for natural products and bio- active compounds.