Premium
Expedient Synthesis of 2‐Iminothiazolidines via Telescoping Reactions Including Iron‐Catalyzed Nitrene Transfer and Domino Ring‐Opening Cyclization (DROC)
Author(s) -
Coin Guillaume,
Ferrier de Montal Oriane,
Dubourdeaux Patrick,
Latour JeanMarc
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001379
Subject(s) - nitrene , aziridine , domino , catalysis , ring (chemistry) , chemistry , combinatorial chemistry , lewis acids and bases , organic synthesis , cascade reaction , organic chemistry
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.