Palladium-catalyzed asymmetric allylic amination of racemic butadiene monoxide with isatin derivatives.

نویسندگان

  • Gen Li
  • Xiangqing Feng
  • Haifeng Du
چکیده

Isatins and their derivatives are important functional moities and building blocks in pharmaceutical and synthetic chemistry. Numerous enantioselective transformations at the C-3 carbonyl group have been well developed. However, the asymmetric substitution reaction with isatins and their derivatives as nucleophiles based on the free N-H groups has been less studied due to the relatively weaker nucleophilicity resulting from the two electron-withdrawing carbonyl groups. In this paper, a palladium-catalyzed asymmetric allylic amination of racemic butadiene monoxide with isatin derivatives using a chiral phosphoramidite olefin hybrid ligand has been successfully developed under mild conditions. A variety of chiral amino alcohols were afforded in 55-87% yields with 10/1->20/1 regioselectivity ratios and 80-97% ees.

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عنوان ژورنال:
  • Organic & biomolecular chemistry

دوره 13 20  شماره 

صفحات  -

تاریخ انتشار 2015