Optically Active Seleninamides: Isolation, Absolute Configuration, and Racemization Mechanism
The Journal of Organic Chemistry2005Vol. 70(3), pp. 868–873
Citations Over Time
Abstract
Optically active seleninamides were obtained for the first time by chromatographic resolution on an optically active column. The absolute configurations of the optically active seleninamides were determined by comparing their chiroptical properties with those of analogous sulfinamides, the stereochemistry of which was determined by transformation into chiral sulfoxides of known configurations. The optically active seleninamides were found to racemize in solution. Kinetic studies of the racemization and theoretical studies clarified that the racemization of the optically active seleninamides in solution proceeds via hypervalent hydrates formed by the reaction with water.
Related Papers
- → Chemoenzymatic Dynamic Kinetic Resolution of Alcohols and Amines(2009)229 cited
- → Aminocyclopentadienyl Ruthenium Chloride: Catalytic Racemization and Dynamic Kinetic Resolution of Alcohols at Ambient Temperature(2002)207 cited
- → Efficient ruthenium-catalyzed racemization of secondary alcohols: application to dynamic kinetic resolution(2002)88 cited
- → Photoactivated Racemization Catalyst for Dynamic Kinetic Resolution of Secondary Alcohols(2010)34 cited
- → Dynamic Kinetic Resolution of rac‐2‐Hydroxy‐1‐indanone by using a Heterogeneous Ru(OH)3/Al2O3 Racemization Catalyst and Lipase(2010)17 cited