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 |
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| Authors: | Palim cio G. Guerrero Jr., Miguel J. Dabdoub,Adriano C.M. Baroni |
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| Affiliation: | aLaboratório de Química Orgânica, Universidade Estadual Paulista, UNESP, Tamekishi Takano, 5, 11900-000 Registro, SP, Brazil;bLaboratório de Compostos Organocalcogênios, Universidade de São Paulo/USP, Av. Bandeirantes, 3900, 14500-000 Ribeirão Preto, SP, Brazil;cLaboratório de Química Farmacêutica, Universidade Federal do Mato Grosso do Sul, UFMS, Campo Grande, MS, Brazil |
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| Abstract: | 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 C4H9TeBr 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 C4H9TeBr. |
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