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Samarium(II) iodide (SmI(2)) is one of the most important reducing agents in organic synthesis. Synthetic chemistry promoted by SmI(2) depends on the efficient and reliable preparation of the reagent. Unfortunately, users can experience difficulties preparing the reagent, and this has prevented realization of the full synthetic potential of SmI(2). To(More)
Recently, samarium(II) iodide reductants have emerged as powerful single electron donors for the highly chemoselective reduction of common functional groups. Complete control of the product formation can be achieved on the basis of a judicious choice of a Sm(II) complex/proton donor couple, even in the presence of extremely sensitive functionalities(More)
A sensitive high-performance liquid chromatographic method for the determination of etodolac in serum was developed. The limit of detection was 0.2 microgram/ml. The specificity of the method was demonstrated by the lack of response obtained with a variety of control sera, sera spiked with etodolac congeners, and sera obtained from rats treated with a(More)
A series of pyrido[3,4-d]azepines that are potent and selective 5-HT2C receptor agonists is disclosed. Compound 7 (PF-04781340) is identified as a suitable lead owing to good 5-HT2C potency, selectivity over 5-HT2B agonism, and in vitro ADME properties commensurate with an orally available and CNS penetrant profile. The synthesis of a novel bicyclic(More)
Herein we describe a strategy for the selective, electron transfer reduction of lactones of all ring sizes and topologies using SmI(2)-H(2)O and a Lewis base to tune the redox properties of the complex. The current protocol permits instantaneous reduction of lactones to the corresponding diols in excellent yields, under mild reaction conditions and with(More)
The single-step synthesis of 3-hydroxy carboxylic acids from readily available Meldrum's acids involves a selective monoreduction using a SmI(2)-H(2)O complex to give products in high crude purity, and it represents a considerable advancement over other methods for the synthesis of 3-hydroxy acids. The protocol includes a detailed guide to the preparation(More)
The first general reduction of nitriles to primary amines under single electron transfer conditions is demonstrated using SmI2 (Kagan's reagent) activated with Lewis bases. The reaction features excellent functional group tolerance and represents an attractive alternative to the use of pyrophoric alkali metal hydrides. Notably, the electron transfer from(More)
A chemoselective switch between reaction pathways by an alcohol cosolvent effect in a general SmI2-mediated synthesis of uracil derivatives is described. The method relies on the use of coordinating solvents to increase the redox potential of Sm(II) and results in a chemoselective 1,2-reduction (SmI2-H2O) or 1,2-migration via in situ generated N-acyliminium(More)