Synthetic applications of the aza-Achmatowicz rearrangement
type: CreativeWork
description: A novel method for the enantioselective synthesis of nitrogen containing compounds has been achieved. The oxidative rearrangement of N-acyl 2-furylamines, termed the Aza-Achmatowicz rearrangement, generates a product with a high density of differentiable functionalities. This characteristic of the product makes it an excellent building block for the synthesis of nitrogenous substances of biomedical interest. Optically pure building blocks are also available via the Aza-Achmatowicz rearrangement. The generation of chirality in the starting furyl derivative is obtained by a simple, inexpensive chemoenzymatic method utilizing papain. The chemical reactivity of these heterocycles has been thoroughly explored, and utilized in the synthesis of (+)-desoxoprosopinine, deoxyazasaccharides, izidinie alkaloid systems, $\beta$-lactams, and unusual amino acids.
abstract: A novel method for the enantioselective synthesis of nitrogen containing compounds has been achieved. The oxidative rearrangement of N-acyl 2-furylamines, termed the Aza-Achmatowicz rearrangement, generates a product with a high density of differentiable functionalities. This characteristic of the product makes it an excellent building block for the synthesis of nitrogenous substances of biomedical interest. Optically pure building blocks are also available via the Aza-Achmatowicz rearrangement. The generation of chirality in the starting furyl derivative is obtained by a simple, inexpensive chemoenzymatic method utilizing papain. The chemical reactivity of these heterocycles has been thoroughly explored, and utilized in the synthesis of (+)-desoxoprosopinine, deoxyazasaccharides, izidinie alkaloid systems, $\beta$-lactams, and unusual amino acids.
author: Hermann, Cynthia Wood
language: eng
keywords: Organic chemistry
date published: 1990
date modified: 2026-07-24T04:10:32Z
provider: Rice University
publisher: Networked Digital Library of Theses and Dissertations
type: WebPage
source organization: Rice University

PropertyValue
property ID: Handle
value: https://hdl.handle.net/1911/16348