4634-89-3Relevant articles and documents
Stereodivergent Total Syntheses of (+)-Monomorine I and (+)-Indolizidine 195B
Dawood, Rafid S.,Stockman, Robert A.
, p. 3850 - 3853 (2021)
A simple and efficient stereoselective total syntheses of two natural products (+)-monomorine I and (+)-indolizidine 195B in high yields starting from a readily available alcohol is described. The key step in this synthetic route exploits the judicious use of solvent to enable a closed or open transition state in a nucleophilic addition of Grignard reagent to sulfinimine, giving selective access to two distinct diastereomers required for the formation of the two target natural products.
A Supramolecular Strategy for Selective Catalytic Hydrogenation Independent of Remote Chain Length
Bender, Trandon A.,Bergman, Robert G.,Raymond, Kenneth N.,Toste, F. Dean
supporting information, p. 11806 - 11810 (2019/08/22)
Performing selective transformations on complex substrates remains a challenge in synthetic chemistry. These difficulties often arise due to cross-reactivity, particularly in the presence of similar functional groups at multiple sites. Therefore, there is a premium on the ability to perform selective activation of these functional groups. We report here a supramolecular strategy where encapsulation of a hydrogenation catalyst enables selective olefin hydrogenation, even in the presence of multiple sites of unsaturation. While the reaction requires at least one sterically nondemanding alkene substituent, the rate of hydrogenation is not sensitive to the distance between the alkene and the functional group, including a carboxylate, on the other substituent. This observation indicates that only the double bond has to be encapsulated to effect hydrogenation. Going further, we demonstrate that this supramolecular strategy can overcome the inherent allylic alcohol selectivity of the free catalyst, achieving supramolecular catalyst-directed regioselectivity as opposed to directing-group selectivity.
Ligand-controlled, tunable silver-catalyzed C-H amination
Alderson, Juliet M.,Phelps, Alicia M.,Scamp, Ryan J.,Dolan, Nicholas S.,Schomaker, Jennifer M.
supporting information, p. 16720 - 16723 (2015/01/16)
The development of readily tunable and regioselective C-H functionalization reactions that operate solely through catalyst control remains a challenge in modern organic synthesis. Herein, we report that simple silver catalysts supported by common nitrogenated ligands can be used to tune a nitrene transfer reaction between two different types of C-H bonds. The results reported herein represent the first example of ligand-controlled and site-selective silver-promoted C-H amination.
