Expedient Synthesis of 2‐Iminothiazolidines via Telescoping Reactions Including Iron‐Catalyzed Nitrene Transfer and Domino Ring‐Opening Cyclization (DROC). Issue 3 (9th December 2020)

• Record Type: Journal Article
• Authors: Coin, Guillaume; de Ferrier de Montal, Oriane; Dubourdeaux, Patrick; Latour, Jean‐Marc
• Is Part Of: European journal of organic chemistry. Issue 3(2021)
• Page Start: 443
• Page End: 448
• Publication Date: 2020-12-09
• Subjects: DROC -- 2-Iminothiazolidines -- Iron catalyst -- Nitrene transfer -- Telescoping catalysis; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202001379
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 2‐iminothiazolidines are important scaffold for pharmaceutical drugs. Herein, we describe a fast and easy procedure for their synthesis by a telescoping reaction integrating an iron‐catalyzed nitrene transfer under mild conditions. The aziridination reaction of olefins is followed by the domino ring‐opening cyclization (DROC) of the aziridine intermediates with organic isothiocyanates catalyzed by a Lewis acid leading to the desired product. This new synthetic route allows time, step and purification economies, which is in agreement with the development of more efficient processes for the synthesis of small molecules. Abstract : In this work, iron‐catalyzed aziridination (nitrene transfer) is combined in a single process to aziridine ring opening (DROC) to produce 2‐iminothiazolidines which constitute interesting cores of pharmaceuticals.