Hydroalumination of selenoacetylenes: a versatile generation and reactions of α-aluminate vinyl selenide intermediates in the highly regio and stereoselective synthesis of telluro(seleno)ketene acetals

✍ Scribed by Palimécio G. Guerrero Jr.; Miguel J. Dabdoub; Adriano C.M. Baroni

• Book ID: 104095337
• Publisher: Elsevier Science
• Year: 2008
• Tongue: French
• Weight: 134 KB
• Volume: 49
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2008.04.072

✦ Synopsis

The hydroalumination of butylseleno acetylenes with DIBAL-H followed by addition of n-butyllithium generated in situ the (Z)butylseleno vinyl alanates intermediates which were captured with C 4 H 9 TeBr furnishing the (E)-telluro(seleno)ketene acetals exclusively. The isomers with opposite stereochemistry (Z)-telluro(seleno)ketene acetals were obtained by the reduction of phenylseleno acetylenes with lithium di-(isobutyl)-n-butyl aluminate hydride (Zweifel's reagent) followed by reaction of (E)-phenylseleno vinyl alanates intermediates with C 4 H 9 TeBr.