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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 183, 2008 - Issue 4
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Original Articles

Selenosilanes Mediated Stereoselective Synthesis of Polyfunctionalized Organic Molecules

Alessandro Degl'Innocenti Università di Firenze, Dipartimento di Chimica Organica and HBL, Sesto Fiorentino, Italy
,
Antonella Capperucci Università di Firenze, Dipartimento di Chimica Organica and HBL, Sesto Fiorentino, Italy
,
Giulio Castagnoli Università di Firenze, Dipartimento di Chimica Organica and HBL, Sesto Fiorentino, Italy
,
Irene Malesci Università di Firenze, Dipartimento di Chimica Organica and HBL, Sesto Fiorentino, Italy
,
Caterina Tiberi Università di Firenze, Dipartimento di Chimica Organica and HBL, Sesto Fiorentino, Italy
&
Brunella Innocenti Università di Firenze, Dipartimento di Chimica Organica and HBL, Sesto Fiorentino, Italy
Pages 966-969 | Published online: 29 Oct 2008
 
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Abstract

Bis(trimethylsilyl)selenide (HMDSS) acts as an efficient reagent in the TBAF catalyzed reaction with different substituted epoxides, episulfides, and aziridines, leading to β -functionalized diselenides in a highly regio- and stereoselective way. When using α -bromo alkyl ethers as trapping agent, 1,3-oxaselenolanes and 1,3-thiaselenolanes can be isolated, while 1,3-selenazolidines could be obtained through reduction of β -amino diselenides followed by in situ treatment with different aldehydes.

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