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

Chemical Science Pub Date: 2020-02-19 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.

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