Β‐N‐Heterocyclic Cyclobutane Carboximides: Synthesis through a Tandem Base‐Catalyzed Amidation/aza‐Michael Addition Protocol and Facile Transformations. Issue 16 (5th April 2023)

• Record Type: Journal Article
• Authors: Barranco, Stefano; Cuccu, Federico; Liu, Dayi; Robin, Sylvie; Guillot, Régis; Secci, Francesco; Brenner, Valérie; Mons, Michel; Caboni, Pierluigi; Aitken, David J.; Frongia, Angelo
• Is Part Of: European journal of organic chemistry. Volume 26:Issue 16(2023)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2023-04-05
• Subjects: carbocycles -- diastereoselectivity -- heterocycles -- small ring systems -- synthetic methods; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202300183
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A stereoselective one‐pot double derivatization of cyclobutene‐1‐carboxylic acid via a mild organic base catalyzed amidation/aza‐Michael addition of benzo[d]oxazol‐2(3H)‐ones has been developed. This unprecedented tandem reaction provides access to novel β‐ N ‐heterocyclic cyclobutane carboximide derivatives with a trans geometry. The carboximide moiety reacts smoothly with nucleophiles, allowing access to diverse derivatives of trans ‐β‐ N ‐heterocyclic cyclobutanecarboxylic acid, including peptidomimetic structures. Abstract : A stereoselective one‐pot double derivatization of cyclobutene‐1‐carboxylic acid via a mild organic base catalyzed amidation/aza‐Michael addition of benzo[d]oxazol‐2(3H)‐ones has been developed.