81580-34-9Relevant academic research and scientific papers
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 (2005)
(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
Step-efficient access to chiral primary amines
Nugent, Thomas C.,Marinova, Sofiya M.
, p. 153 - 166 (2013/02/25)
Routes to enantioenriched amines are outlined that employ reductive amination and carbanion addition methods. The strategies require either one or two reaction steps from prochiral carbonyl compounds for the synthesis of the corresponding chiral primary amines. Georg Thieme Verlag Stuttgart New York.
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
, 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.
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.
SYNTHESIS OF AMINE STEREOISOMERS
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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.
