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Download Electrochemistry of Organic Compounds by Walther L. PDF

By Walther L.

Oxidations, rate reductions, and miscellaneous ameliorations of natural compounds with electrical energy in resolution and through silent electrical discharge.

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SOC. 1992, 114, 2755. Chemical Company, Morton Grove, IL [19] M. P. Doyle, A. v. Oeveren, L. J. Westrum, 60053, USA). M. N. Protopopova, T. W. , J. Am. Chem. 1991, 113, 8982. 1998 Oxazaborolidines and Dioxaborolidines in Enantioselective Catalysis B. B. Lohray, and Vidya Bhushan During the last decade, use of oxazaborolidines and dioxaborolidines in enantioselective catalysis has gained importance. [ 1, 21 One of the earliest examples of oxazaborolidines as an enantioselective catalyst in the reduction of ketonedketoxime ethers to secondary alcohols/amines was reported by Itsuno et al.

Larcheveque and coworkers reported on the deprotonation of N-acyl-ephedrines with LDA in the presence of hexamethylphosphoric acid triamide (HMPA) and subsequent reactions with alkyl halides providing products with diastereoselectivities of c 80 : 20. Only when MgC12 was added, diastereomeric ratios of > 95 : 5 were achieved (Scheme 3). How can the effects brought about by the addition of metal salts be explained? Since the start of investigations into asymmetric reactions with enolates it has been known that the reactivity and selectivity observed in enolate chemistry is influenced not only by the base employed, but also by the use of cosolvents such as HMPA, and the addition of metal salts or Lewis acids.

13] Vinyl ethers, which are more reactive than their thioether counterparts, undergo ene reactions with high enantioselectivities using (R)-3 as catalyst. [14] Thus, addition of 2phenoxybutene to chloroacetaldehyde in the presence of 10 mol% of (R)-3 gives the corresponding ene product in 53 % yield with 97 % ee (Scheme 4). [14] The impressive levels of stereocontrol obtained with this methodology have led to a number of concise syntheses [ l ] of important bioactive targets. Recent studies by the Mikami group include the development of a new synthetic route to insect pheremones using isoprene as the ene component, [15] the preparation of two fragments of the immunosuppressant rapamycin, [ 161 and the synthesis of prostacyclin analogues including isocarbacyclin.

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