Synthesis of Heterocycles by isothiourea organocatalysis |
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Authors: | Anup Biswas Haripriyo Mondal Modhu S Maji |
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Institution: | 1. Department of Chemistry, Hooghly Women's College, Hooghly, India;2. Department of Chemistry, Indian Institute of Technology, Kharagpur, India |
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Abstract: | Isothiourea was first employed as catalyst by Birman in 2006 for the enantioselective acyl transfer reaction. The catalyst was then well explored in the course of kinetic resolution and desymmetrization studies. A few years later, Romo and Smith applied isothiourea catalysis in enantioselective cascade reactions to prepare carbocycles and heterocycles acessing new reactivities of isothiourea. Several research groups were then attracted toward this new field of organocatalysis, and applied isothioureas as nucleophilic catalysts in executing cascade methodologies to synthesize various intresteting molecular scaffolds including heterocycles. The present review documents a summary on the construction of heterocyclic molecules by isothiourea organocatalysis. Heterocycles are of prime interest to organic chemists due to their omnipresence in natural products and bioactive molecules. The Lewis basic nucleophilic catalyst isothioureas play a pivotal role in the cascades to generate either α,β-unsaturated acyl isothiouronium ion or isothiouronium enolate as the prime reaction intermediate. We have covered the reactions involving two intermediates of opposite reactivities affording various heterocycles. |
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