Fe-Catalyzed Amidation of Allylic Alcohols by Borrowing Hydrogen Catalysis

Allylic amines are useful building blocks in organic synthesis, so the development of green and efficient methods for the preparation of allylic amines are of great importance. An Fe-catalyzed amidation of allylic alcohols with chiral tert-butylsulfinamide has been developed. With water as the only by-product, a range of synthetically useful chiral sulfinamide olefin derivatives (30 examples) were obtained under mild reaction conditions. The reaction can be performed on a gram-scale, and the products could serve as chiral ligands for asymmetric catalysis. Mechanistic studies suggest that the reaction proceeds by an Fe-catalyzed borrowing hydrogen process, which is different from most of the reported allylic amination reactions.

Automated summary

A Fe-catalyzed amidation of allylic alcohols with chiral tert-butylsulfinamide has been developed for the synthesis of chiral sulfinamide olefin derivatives. The reaction proceeds under mild conditions with water as the only by-product.