Description

• General description: Stannic chloride (SnCl4) is a strong Lewis acid widely used as a promoter or catalyst in organic synthesis. It is soluble in most organic solvents.[1]
• Application: Stannic chloride can be used to catalyze:Cyclization of trans β-monocyclohomofarnesic acid to form norambreinolide.[2]Formation of C-glycosides of aromatic compounds such as thiophene, naphthalene and phloroglucinol trimethyl ether.[3]Formal [4+2] cycloaddition of 3-ethoxycyclobutanones and allyltrialkylsilanes to form 3-ethoxy-5-[(trialkylsilyl)methyl]cyclohexan-1-ones.[4]Diastereoselective reaction of δ-alkoxyallylstannanes with aldehydes to form 1,5-diol derivatives.[5]Other applications of SnCl4:The SnCl4-2,6-dialkoxyphenols complexes can catalyze cyclization of poylenes, such as 4-(homogeranyl)toluene to form trans-fused tricyclic compound.[6]SnCl4 can act as a promoter during the reaction of ortho-aminobenzonitriles with β-ketoesters and β-enaminonitriles to form 4-aminoquinolines and 4-aminopyridines, respectively.[7]SnCl4-silver perchlorate forms an effective catalytic system for the stereoselective of glycosylation 1-O-acetyl glucose.[8]