Unusual Cycloaddition Reactions of Substituted-N-(arylsulfonyl)aziridines with Aryl and Alkyl Isothiocyanates in the Presence of Sodium Iodide as Catalyst

“On Water”: Efficient Iron‐Catalyzed Cycloaddition of Aziridines with Heterocumulenes

“…The [3+2] cycloaddition reaction of aziridines with heterocumulenes provides a powerful tool to access a wide range of functionalized fivemembered heterocycles that exhibit interesting biological and medicinal properties. [4] Thus, the cycloaddition of aziridines with carbodiimides, [5] isocyanates, [5][6][7][8] and isothiocyanates [5,7,[9][10][11] has been studied employing Pd, [5] Ni, [6] HBF 4 , [7] Mg-MeOH, [8] PBu 3 , [9] NaI [10] or Ph 4 SbBr [11] -based systems as either the catalyst or stoichiometric reagent. These reactions are effective in an organic medium and generally involve an inert atmosphere.…”

Solid solution of two diastereomers of [3a(R,S),7a(R,S)]-3-[(1′R)-1-phenylethyl]perhydro-1,3-benzothiazol-2-iminium chloride

“…Substituted 1,3-thiazolidines have also been explored as valuable starting materials for the preparation of more complex structures (Zask et al, 1990;Hwu et al, 1999;Jin & Kim, 2002). The most popular method to synthesize thiazolidines is the cyclization reaction of aziridines with heterocumulenes, such as phenyl isothiocyanate, in the presence of a catalyst [NaI; Campbell & Craig, 1980;Nadir & Basu, 1995; compounds of palladium(II); Baeg et al, 1995;Butter et al, 2000; or Bu 3 P; Wu et al, 2008]. Also, the thiocyanate ion was found to react with aziridines with Bu 4 NHSO 4 as the catalyst to give a five-membered thiazoline structure (Weitzberg et al, 1984).…”

Highly Enantioselective Synthesis of 1,3-Oxazolidin-2-imine Derivatives by Asymmetric Cycloaddition Reactions of Vinyloxiranes with Unsymmetrical Carbodiimides Catalyzed by Palladium(0) Complexes

“…Asymmetric synthesis is an important strategy for the preparation of enantiomerically pure or enriched compounds . The cycloaddition and ring expansion reactions of three-membered-ring heterocycles such as aziridines and oxiranes with heterocumulenes to form five-membered ring products have been widely studied in the past several years. For example, some 2-oxazolidine derivatives have been prepared which may have interesting biological activities .…”