An Efficient Synthetic Method of Aliphatic Selenoamides via Selenoketene Intermediates

MeOTf-Mediated Alkynylation of Selenoamides Leading to β-Methylselenenyl α,β-Unsaturated Ketones and Their Characterization

“…Considerable attention has been paid to the chemistry of organoselenium compounds because of their value as synthetic reagents and their possible biological application . In the course of our studies on selenocarbonyl compounds, we previously reported efficient methods for the synthesis of aliphatic selenoamides and the conversion of α,α-disubstituted selenoamides with organolithium reagents to asymmetrical ketones . We further found that the reaction of selenoamides with lithium acetylide derived from (trimethylsilyl)acetylene and methyl iodide gives β-methylselenenyl α,β-unsaturated ketones .…”

Synthesis and Applications of Chalcogenoamide: Thio-, Seleno- and Telluroamides

“…The primary selenoamides are prepared by reaction of nitriles with appropriate selenating reagents such as phosphorus (V) selenide (P 2 Se 5 ), hydrogen selenide (H 2 Se), Al 2 Se 3 , NaSeH, tris(trimethylsilyl)monoselenophosphate or potassium selenobenzoate [86][87][88][89][90] (Scheme 32). R As other preparation methods of secondary and tertiary selenoamides 57, a combination of lithium alkyneselenolates and amines, one of aromatic diselenoic acid Se-methyl esters and amines, or dihalomethane with elemental selenium, NaH and amines have been established [96][97][98][99][100][101][102][103][104] (Scheme 34).…”

Michael Addition of Selenoamides to α,β-Unsaturated Carbonyl Compounds: Stereocontrolled Synthesis of δ-Oxo Selenoamides and Their Reactivity

“…However, the recent development of new synthetic methods for selenocarbonyl compounds and the increasing attention to organoselenium compounds stimulated us to explore the utility of lithium eneselenolates as a carbon nucleophile to Michael acceptors. Very recently, we have established a one-pot synthetic procedure of selenoamides 1 and found that their lithium eneselenolates 2 reacted with aldehydes to afford α,β-unsaturated selenoamides . Herein, we report the stereocontrolled Michael addition of lithium eneselenolates to α,β-unsaturated esters and ketones leading to δ-oxo selenoamides and their reactivity.…”