Sequential reductive amination-hydrogenolysis: A one-pot synthesis of challenging chiral primary amines
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
Nugent, Thomas C.,Negru, Daniela E.,El-Shazly, Mohamed,Hu, Dan,Sadiq, Abdul,Bibi, Ahtaram,Umar, M. Naveed
p. 2085 - 2092
(2011/10/19)
Aliphatic lmines in titanium-mediated reductive cross-coupling: unique reactivity of Ti(O-i-Pr)-BuLi
A procedure for the coupling of aliphatic lmlnes with allyllc and alienle alkoxldes Is described. The success of these studies was enabled by a unique reactivity profile of TI(IV) IsopropoxIde/n-BuLI compared to well-known TI(IV) IsopropoxIde/RMgX systems
Tarselli, Michael A.,Mlcalizio, Glenn C.
supporting information; experimental part
p. 4596 - 4599
(2009/12/09)
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