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Amide reduction with borane mechanism

Two possible transition states of amide reduction were found.
Borane-tetrahydrofuran (bthf) and borane-dimethyl sulfide (BMS, dmsb) are often used as code promo valides chez esprit a borane source.
The method is applicable to primary, secondary, tertiary, and aromatic amines, and the mildness of the reaction conditions allows preservation of otherwise labile functional groups.
Volatility and flammability are always a drawback.
Seebach, Dieter; Kalinowski, Hans-Otto; Langer, Werner; Crass, Gerhard; Wilka, Eva-Maria (1983).#960 electrons from the CN move to the cationic N neutralising the charge creating the amine product.The reaction pathways were searched by intrinsic reaction coordinate analysis.The most interesting application is as a borane source for oxazeborolidine catalyzed asymmetric reductions of ketones (.This unprecedented regioselective oxidative process employs tbhp and Et3N in stoichiometric amounts under metal-free conditions in dmso as solvent.BMS is more stable than bthf but has an unpleasant odor.R, R' or, r" may be either alkyl or aryl substituents.Have questions or comments?They offer interesting applications in the reduction of various functional groups.Note that this reaction is different to that of other, cO compounds which reduce to alcohols.Lett., 2001, 3, 465-467.

Amide reduction, amide reduction to amine.
Step 2: The tetrahedral intermediate collapses and displaces the O as part of a metal alkoxide leaving group, this produces a highly reactive iminium ion an intermediate.
The presence of complexing groups sometimes leads to borane adducts.
Ian Hunt, Department of Chemistry, University of Calgary.Highly regioselective ring opening of epoxides with poor nucleophiles such as indole, borane, O -trimethylsilylhydroxylamine, p -nitroaniline and sterically hindered tert -butylamine is a fast and convenient reaction in the presence.0 M lithium perchlorate-Et2O solution (lpde).The catalytic asymmetric borane reduction of both electron-deficient and electron-rich ketones was achieved with high enantioselectivity with a C3-symmetric chiral tris(-hydroxy phosphoramide) ligand.Step 1: The nucleophilic, h from the hydride reagent adds to the electrophilic.Reactions usually in Et2O or THF followed by H3O work-ups.Acyloxyketones can be converted in situ to monoprotected diol derivatives in excellent yields upon treatment with BH3SMe2.Name Reactions, corey-Bakshi-Shibata Reduction.1 M in THF and are therefore easier to handle than diborane.

New York: Wiley, isbn Cope, Arthur.; Ciganek, Engelbert (1959).
In the potential mechanism note that it.
Chapter 20: Carboxylic Acid Derivatives.