10315-85-2Relevant articles and documents
Asymmetric Kulinkovich Hydroxycyclopropanation of Alkenes Mediated by Titanium(IV) TADDOLate Complexes
Iskryk, Marharyta,Barysevich, Maryia,O?eka, Maksim,Adamson, Jasper,Kananovich, Dzmitry
, p. 1935 - 1948 (2019)
Asymmetric Kulinkovich cyclopropanation of carboxylic esters with prochiral alkenes is reported. The process is mediated by titanium(IV) (4 R,5 R)-TADDOLate complexes and affords correspondingly (Z)- or (E)-cyclopropanols with up to 84-87% ee in the event of intra- or intermolecular olefin ligand exchange in intermediate titanacyclopropane [titanium(II)-alkene] species. Configuration of the olefin double bond is preserved in the cyclopropane products, pointing out on total retention of configuration at Ti-C bond in the cyclopropane forming step. The results have been interpreted in the framework of ate complex mechanism, suggesting formation of pentacoordinated titanium ate species as a prerequisite of high enantiocontrol.
TEMPO-Catalyzed Oxidative Amidation of Alcohols via Hexafluoroisopropyl Esters
Vatèle, Jean-Michel
supporting information, p. 2280 - 2284 (2015/09/28)
Stepwise oxidative amidation of alcohols using trichloroisocyanuric acid, a catalytic amount of TEMPO in combination with pyridine and hexafluoroisopropyl (HFIP) alcohol followed by amines is described. This procedure used HFIP esters as activating esters which were found to be very efficient acylating agents for amide bond formation. This process is compatible with a number of functional groups and acid-sensitive protecting groups.
Aerobic oxidation of NHC-catalysed aldehyde esterifications with alcohols: Benzoin, not the Breslow intermediate, undergoes oxidation
Delany, Eoghan G.,Fagan, Claire-Louise,Gundala, Sivaji,Zeitler, Kirsten,Connon, Stephen J.
, p. 6513 - 6515 (2013/07/26)
Benzoin (and neither the Breslow intermediate nor the NHC-aldehyde tetrahedral adduct) has been unambiguously identified as the oxidised species in aerobic NHC-catalysed aldehyde esterifications.
