826-16-4Relevant 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
Asymmetric intermolecular hydroamination of unactivated alkenes with simple amines
Reznichenko, Alexander L.,Nguyen, Hiep N.,Hultzsch, Kai C.
supporting information; experimental part, p. 8984 - 8987 (2011/02/21)
A hard nut to crack: The asymmetric intermolecular Markovnikov addition of simple amines to unactivated alkenes can be achieved utilizing binaphtholate rare-earth-metal catalysts with up to 61% ee and 73% de in the case where R 2 contains a stereogenic center.
SYNTHESIS OF AMINE STEREOISOMERS
-
Page/Page column 25-26, (2008/06/13)
The invention relates to methods for producing secondary and tertiary amine diastereomers and corresponding enantiopure or enantioenriched primary or secondary chiral amine products.
Reversal of diastereofacial selectivity in hydride reductions of N-tert-butanesulfinyl imines
Colyer, John T.,Andersen, Neil G.,Tedrow, Jason S.,Soukup, Troy S.,Faul, Margaret M.
, p. 6859 - 6862 (2007/10/03)
A variety of N-tert-butanesulfinyl imines were reduced with NaBH 4 in THF containing 2% water to provide the corresponding secondary sulfinamides in high yield and diastereoselectivity. By using the same sulfinyl imine starting materials and changing the reductant to L-Selectride, the stereoselectivity could be efficiently reversed to afford the opposite product diastereomer in high yield and selectivity.
Evolution of titanium(IV) alkoxides and Raney Nickel for asymmetric reductive amination of prochiral aliphatic ketones
Nugent, Thomas C.,Wakchaure, Vijay N.,Ghosh, Abhijit K.,Mohanty, Rashmi R.
, p. 4967 - 4970 (2007/10/03)
(Chemical Equation Presented) A new method for the one-pot asymmetric reductive amination of prochiral aliphatic ketones has been developed. The previously unexplored reagent combination of Ti(OiPr) 4/Raney Ni/H2 in the pr
Analgesic dipeptide amides and method of use and composition thereof
-
, (2008/06/13)
A genus of dipeptide amides including as the preferred subgenus the dipeptide amides having the structural formula HTyrD-AlaNR2 R3 wherein R2 is phenylalkyl or substituted-phenylalkyl and R3 is hydrogen, alkyl, phenylalkyl, substituted-phenylalkyl or X-alkyl wherein X is an electronegative moiety are prepared by condensing the dipeptide with the amine or the amino acid with the amino acid amide and are useful as analgesics.
