140707-01-3Relevant academic research and scientific papers
Photodecarboxylative Amination of Redox-Active Esters with Diazirines
Maharaj, Vishala,Chandrachud, Preeti P.,Che, Wen,Wojtas, Lukasz,Lopchuk, Justin M.
supporting information, p. 8838 - 8842 (2021/11/24)
Diazirines have been recently demonstrated to serve as electrophilic amination reagents that afford diaziridines, versatile heterocycles that are readily transformed into amines, hydrazines, and nitrogen-containing heterocycles. Here, we report the photodecarboxylative amination of redox-active esters with diazirines using inexpensive photoactivators under mild conditions with an enhanced scope for primary substrates. The stability of diazirines to blue light is demonstrated, paving the way for further research into other photochemical amination methods with these unique heterocycles.
Further Reactions of t-Butyl 3-Oxobutanthioate and t-Butyl 4-Diethylphosphono-3-oxobutanthioate: Carbonyl Coupling Reactions, Amination, Use in The Preparation of 3-Acyltetramic Acids and Application to The Total Synthesis of Fuligorubin A.
Ley, Steven V.,Smith, Stephen C.,Woodward, Peter R.
, p. 1145 - 1174 (2007/10/02)
Key words: Acyltetramic acid; Phosphonate; Wadsworth-Emmons; Dieckmann cyclisation; Fuligorubin A. Abstract: The use of t-butyl-3-oxobutanthioate (1) and t-butyl 4-diethylphosphono-3-oxobuthanthioate (2) for the preparation of homologated derivatives suitable for amination in the presence of silver(I) trifluoroacetate to afford the corresponding β-ketoamides is discussed.In particular Wadsworth-Emmons coupling reactions of (2) with various carbonyl compounds gave good yields of E-substituted products.Many of the β-ketoamides were shown to be suitable precursors for 3-acyltetramic acids using a Dieckman cyclisation with tetra-n-butyl ammonium fluoride as the cyclising base.These new reactions were applied to the total synthesis of the polyene 3-acyltetramic acid fuligorubin A.
