Synthesis, Table of Contents Synthesis 2018; 50(06): 1199-1208DOI: 10.1055/s-0037-1609202 short review © Georg Thieme Verlag Stuttgart · New YorkApplication of Trimethylsilanolate Alkali Salts in Organic Synthesis Kristýna Bürglová a Institute of Molecular and Translation Medicine, Faculty of Medicine and Dentistry, Palacký University, Hněvotínská 5, 779 00 Olomouc, Czech Republic , Jan Hlaváč * b Department of Organic Chemistry, Faculty of Science, Palacký University, 771 46 Olomouc, Czech Republic Email: jan.hlavac@upol.cz› Author AffiliationsRecommend Article Abstract Buy Article All articles of this category Abstract Trimethylsilanolate alkali salts are widely used in organic synthesis, mainly due to their solubility in common organic solvents. They are frequently used as nucleophiles in ester hydrolysis, both in solution and solid-phase chemistry. However, they have also been used as mild bases or as specific reagents in some chemical transformations. Reactions employing trimethylsilanolate alkali salts as the key component are typically performed under mild reaction conditions. This review summarizes the utilization of trimethylsilanolate alkali salts in various organic transformations. 1 Introduction 2 Properties of Alkali Metal Trimethylsilanolates (TMSO[M]) 3 Trimethylsilanolate Alkali Salts in Organic Synthesis 4 Conclusion Key words Key wordstrimethylsilanolate - ester hydrolysis - cleavage - alkali metals - coupling promoter - solid-phase chemistry - synthesis Full Text References References 1 Ladenburg A. Justus Liebigs Ann. Chem. 1872; 164: 300 2 Sommer LH. Pietrusza EW. Whitmore FC. J. Am. Chem. Soc. 1946; 68: 2282 3 Sommer LH. Green LQ. Whitmore FC. J. Am. Chem. Soc. 1949; 71: 3253 4 Schmidbaur H. Schmidt M. J. Am. Chem. Soc. 1962; 84: 3600 5 Andrianov KA. Alanichev VN. Tikhonov VS. Zh. Obshch. Khim. 1968; 38: 1402 6 Seyferth D. Alleston DL. Inorg. Chem. 1963; 2: 417 7 Schmidbaur H. Perez-Garcia JA. Arnold HS. Z. Anorg. 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