A. Gaumont, M. Gulea, Jocelyne Levillain
Jan 20, 2009
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Influential Citations
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Chemical reviews
Abstract
Heterocyclic compounds are of outstanding importance as pharmaceuticals, agrochemicals, fine and bulk chemicals, and ligands for catalysis.1 Among the different heterocycles, 2-oxazolines have been widely studied and reviewed,2 especially chiral oxazolines3 and bis(oxazolines),4 due to their wide application as ligands for asymmetric catalysis. Compared to 2-oxazolines, the sulfur analogues, that is, the 2-thiazolines, have received less attention. To the best of our knowledge, there is only one review, published by Fustero et al. in 2001,5 which focuses on the preparation and to some extent synthetic applications of both 2-alkyl2-thiazolines and 2-alkyl-2-oxazolines. Recently, various groups have paid attention to the chemical properties of 2-thiazolines, mainly because of the unique properties of sulfur. In different reports, a reactivity that often dramatically differs from that of the corresponding oxazoline derivatives was pointed out. In this contribution, we wish to give an overview of the chemistry of 2-thiazolines, including new methodologies for their preparation, and recent applications, such as their growing use in organic synthesis in the biological field and asymmetric catalysis as ligands. The methods enabling access to thiazolines will first be underlined. Then the reactivity and applications in the fields of organic synthesis, biomolecules (natural or not), and catalysis will be documented. The structure of the thiazolines treated in this review is illustrated in Figure 1. Compounds bearing atoms other than carbon at the 2-position, including 2-H-thiazolines, 2-aminothiazolines, or 2-halogenothiazolines, are beyond the scope of this review. Cited references are restricted to journals, reviews, and books. Literature coverage for this review extends up to September 2007.