73839-93-7Relevant academic research and scientific papers
Sequential reductive amination-hydrogenolysis: A one-pot synthesis of challenging chiral primary amines
Nugent, Thomas C.,Negru, Daniela E.,El-Shazly, Mohamed,Hu, Dan,Sadiq, Abdul,Bibi, Ahtaram,Umar, M. Naveed
supporting information; experimental part, p. 2085 - 2092 (2011/10/19)
Difficult-to-access chiral primary amines were formed in good to high yield and ee using a rare example of a one-pot synthesis from prochiral ketones (sequential reductive amination-hydrogenloysis). As a highlight we also demonstrate a one-pot reductive amination-hydrogenolysis-reductive amination (five reactions) of ortho-methoxyacetophenone resulting in the chiral diamine 1-(2-methoxyphenyl)ethyl-(2-pyridylmethyl)-amine (4) (58% overall yield, >99% ee), a new organocatalyst for aqueous enantioselective aldol reactions. Copyright
Mild and efficient deprotection of the amine protecting p-methoxyphenyl (PMP) group
Verkade, Jorge M.M.,van Hemert, Lieke J.C.,Quaedflieg, Peter J.L.M.,Alsters, Paul L.,van Delft, Floris L.,Rutjes, Floris P.J.T.
, p. 8109 - 8113 (2007/10/03)
Mild and efficient procedures for deprotection of the amine nitrogen protecting p-methoxyphenyl (PMP) group are described. Periodic acid and trichloroisocyanuric acid (TCCA) were found to be particularly effective in realizing amine liberation using 1 and 0.5 equiv of the oxidant, respectively. Extension of the periodic acid-mediated conditions to simultaneous alcohol oxidation by combination with a catalytic amount of sodium dichromate led to smooth conversion of PMP-protected Mannich products into the corresponding β-amino acids in a one-pot procedure.
Hydrazines and azides via the metal-catalyzed hydrohydrazination and hydroazidation of olefins
Waser, Jerome,Gaspar, Boris,Nambu, Hisanori,Carreira, Erick M.
, p. 11693 - 11712 (2007/10/03)
The discovery, study, and implementation of the Co- and Mn-catalyzed hydrohydrazination and hydroazidation reactions of olefins are reported. These reactions are equivalent to direct hydroaminations of C-C double bonds with protected hydrazines or hydrazoic acid but are based on a different concept in which the H and the N atoms come from two different reagents, a silane and an oxidizing nitrogen source (azodicarboxylate or sulfonyl azide). The hydrohydrazination reaction using di-tert-butyl azodicarboxylate is characterized by its ease of use, large functional group tolerance, and broad scope, including mono-, di-, tri-, and tetrasubstituted olefins. Key to the development of the hydroazidation reaction was the use of sulfonyl azides as nitrogen sources and the activating effect of tert-butyl hydroperoxide. The reaction was found to be efficient for the functionalization of mono-, di-, and trisubstituted olefins, and only a few functional groups are not tolerated. The alkyl azides obtained are versatile intermediates and can be transformed to the free amines or triazoles without isolation of the azides. Preliminary mechanistic investigations suggest a rate-limiting hydrocobaltation of the alkene, followed by an amination reaction. Radical intermediates cannot be ruled out and may be involved.
