Stereospecific Interconversion between cis and trans 2,3-Epoxysulfides

✍ Scribed by Atsushi Hirai; Terumichi Tonooka; Kofumi Wakatsuki; Keiji Tanino; Masaaki Miyashita

• Publisher: John Wiley and Sons
• Year: 2002
• Tongue: English
• Weight: 74 KB
• Volume: 114
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/1521-3757(20020301)114:5<847::aid-ange847>3.0.co;2-w

✦ Synopsis

Ring-opening reactions of epoxides with nucleophiles provide a useful method for the stereoselective synthesis of organic compounds. [1] In this type of transformation, the relative stereochemistry of the products reflects that of the parent epoxides, which are usually prepared in the cis or trans forms from the corresponding Z or E olefins, respectively. [2] In this connection, however, the interconversion between the cis and trans epoxides, which contrasts with the configurational isomerization of olefins that is possible by some methods, has not been reported. [3] Recently, Saigo and co-workers and our group have independently reported that the reaction of a 1-(phenylthio)-2,3-epoxyalkane with an organoaluminum reagent resulted in regio-and stereoselective substitution at C2, with double inversion of configuration (Scheme 1). [4, 5]