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

Guerrero, Palimclo G. [UNESP]Dabdoub, Miguel J.Baroni, Adriano C. M.2014-05-202014-05-202008-06-09Tetrahedron Letters. Oxford: Pergamon-Elsevier B.V. Ltd, v. 49, n. 24, p. 3872-3876, 2008.0040-4039http://hdl.handle.net/11449/110The 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. (c) 2008 Elsevier Ltd. All rights reserved.3872-3876engHydroalumination of seleno acetylenes: a versatile generation and reactions of alpha-aluminate vinyl selenide intermediates in the highly regio and stereoselective synthesis of telluro(seleno)ketene acetalsArtigo10.1016/j.tetlet.2008.04.072WOS:000256500500009Acesso restrito