N-Nosyl-O-bromoethyl hydroxylamine acts as a multifunctional formaldehyde, formaldimine, and 1,2-oxazetidine surrogate for C-C and C-O bond-forming reactions

摘要

We describe that N-nosyl-O-bromoethyl hydroxylamine, a bench stable solid, could function as a novel formaldehyde, formaldimine, and 1,2-oxazetidine surrogate under DBU basic conditions. By merely using this simple reagent, a broad range of synthetically useful alpha-hydroxymethyl and alpha-aminomethyl ketones, as well as chiral alpha-alkoxyl and alpha-aminomethyl indanone carboxylates could be divergently obtained via chemo- and stereoselective aldol, Mannich or umpolung C-O bond-forming reactions. The challenging catalytic asymmetric Mannich reaction of formaldimine equivalent was also realized with moderate enantioselectivities.