Issue 18, 2021

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

Abstract

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 α-hydroxymethyl and α-aminomethyl ketones, as well as chiral α-alkoxyl and α-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.

Graphical abstract: 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

Supplementary files

Article information

Article type
Research Article
Submitted
13 May 2021
Accepted
12 Jul 2021
First published
13 Jul 2021

Org. Chem. Front., 2021,8, 5124-5129

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

B. Wu, X. Wen, H. Chen and L. Hu, Org. Chem. Front., 2021, 8, 5124 DOI: 10.1039/D1QO00748C

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