Synthesis and Cleavage of Lactones and Thiolactones. Applications in Organic Synthesis. A Review

One-Pot Double Modification of Polymers Based on Thiolactone Chemistry

“…Hydrolysis and alcoholysis are only significant in basic medium, and aminolysis requires no additives. Aminolysis can thus be performed in aqueous medium, although hydrolysis is an important side reaction [92,108,109]. No reports of thiolysis of γ-thiolactones have been found so far, whereas thiolactones, having smaller and larger ring sizes, are susceptible to nucleophilic attack by a thiolate anion [108,[110][111][112].…”

“…As an alternative to this sequential hydrolysis and conjugate addition (thio-Michael addition), the lysis of thiolactones under basic conditions is often carried out in the presence of an alkylating agent. Because of the high nucleophilic character of the liberated thiol, S-alkylated compounds are the final products of these reactions [108]. Methanolysis of homocysteine-γ-thiolactone hydrochloride 1.HCl and subsequent alkylation by treatment with an alkyl halide in a one-pot fashion has been reported as a simple method for the synthesis of Salkylhomocysteines 5 (Scheme 3b) [114,115].…”

Protected thiol strategies in macromolecular design

“…Thiolactones [226,227] are cyclic thioesters, which can be subdivided into β-, γ-and δ-thiolactones, referring to the number of atoms in the ring structure. The most important class with respect to availability and synthetic applicability are the five-membered γ-thiolactones.…”

5‐exo versus 6‐endo Thiyl‐Radical Cyclizations in Organic Synthesis

“…Thiolactones have proven highly valuable in synthesis and biology . The synthesis of thiolactones has been an area of interest for synthetic chemists for well over a century, with attention being reinvigorated recently . Unlike their homologues, lactones, the strategies that have thus far been developed for the synthesis of thiolactones are somewhat limited and underexamined .…”