4 research outputs found
Protecting-Group-Free Synthesis of Amines: Synthesis of Primary Amines from Aldehydes via Reductive Amination
No full textNew methodology for the protecting-group-free synthesis of primary amines is presented. By optimizing the metal hydride/ammonia mediated reductive amination of aldehydes and hemiacetals, primary amines were selectively prepared with no or minimal formation of the usual secondary and tertiary amine byproduct. The methodology was performed on a range of functionalized aldehyde substrates, including in situ formed aldehydes from a Vasella reaction. These reductive amination conditions provide a valuable synthetic tool for the selective production of primary amines in fewer steps, in good yields, and without the use of protecting groups
Stereoselective Total Synthesis of Aminoiminohexitols via Carbamate Annulation
No full textNew methodology for the preparation of a variety of aminoiminohextitols
is described. Key in the synthesis is the application of a diastereoselective
Strecker reaction and the extension of our carbamate annulation methodology
to protected and functionalized alkenylamines. Insight into the effects
that the substitution patterns of the alkenylamines have on the diastereoselectivity
of the iodocyclization and carbamate annulation is discussed. An evaluation
of the glycosidase inhibitory activity of the aminoiminohexitols and
derivatives is also presented, with the previously undisclosed d-talo isomer showing good selective inhibition
of β-d-glucosidase
Stereoselective Total Synthesis of Aminoiminohexitols via Carbamate Annulation
No full textNew methodology for the preparation of a variety of aminoiminohextitols
is described. Key in the synthesis is the application of a diastereoselective
Strecker reaction and the extension of our carbamate annulation methodology
to protected and functionalized alkenylamines. Insight into the effects
that the substitution patterns of the alkenylamines have on the diastereoselectivity
of the iodocyclization and carbamate annulation is discussed. An evaluation
of the glycosidase inhibitory activity of the aminoiminohexitols and
derivatives is also presented, with the previously undisclosed d-talo isomer showing good selective inhibition
of β-d-glucosidase
Stereoselective Total Synthesis of Aminoiminohexitols via Carbamate Annulation
No full textNew methodology for the preparation of a variety of aminoiminohextitols
is described. Key in the synthesis is the application of a diastereoselective
Strecker reaction and the extension of our carbamate annulation methodology
to protected and functionalized alkenylamines. Insight into the effects
that the substitution patterns of the alkenylamines have on the diastereoselectivity
of the iodocyclization and carbamate annulation is discussed. An evaluation
of the glycosidase inhibitory activity of the aminoiminohexitols and
derivatives is also presented, with the previously undisclosed d-talo isomer showing good selective inhibition
of β-d-glucosidase
