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Synthesis 2023; 55(10): 1507-1516
DOI: 10.1055/a-2029-0015
DOI: 10.1055/a-2029-0015
feature
Hetero-Diels–Alder Addition of Ethyl 2-Nitrosoacrylate to (Z)-Prop-1-enyl Ethers. Stereoselective Synthesis of a Precursor to Sacubitril
This research has been co-financed by the European Union and Greek national funds through the Operational Program Competitiveness, Entrepreneurship and Innovation, under the call RESEARCH–CREATE–INNOVATE (project code: T1EDK-01161).
Abstract
A novel, conceptually distinct synthesis of a key precursor to sacubitril, an antihypertensive drug, is presented. The well-demonstrated hetero-Diels–Alder addition of in situ generated nitrosoalkenes to electron-rich enol ethers was engaged to establish the required functionalities with controllable relative stereochemistry. An asymmetric variant of the enol ether enabled access to the target molecule in enantiopure form.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2029-0015.
- Supporting Information
Publication History
Received: 09 January 2023
Accepted after revision: 06 February 2023
Accepted Manuscript online:
06 February 2023
Article published online:
15 March 2023
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