Chiral N, N'-dioxide/Mg(OTf)2 complex-catalyzed asymmetric [2,3]-rearrangement of in situ generated ammonium salts

Chem Sci. 2020 Feb 19;11(11):3068-3073. doi: 10.1039/c9sc06342k.

Abstract

Catalytic enantioselective [2,3]-rearrangements of in situ generated ammonium ylides from glycine pyrazoleamides and allyl bromides were achieved by employing a chiral N,N'-dioxide/MgII complex as the catalyst. This protocol provided a facile and efficient synthesis route to a series of anti-α-amino acid derivatives in good yields with high stereoselectivities. Moreover, a possible catalytic cycle was proposed to illustrate the reaction process and the origin of stereoselectivity.