97011-89-7Relevant articles and documents
Core-Shell Composite as the Racemization Catalyst in the Dynamic Kinetic Resolution of Secondary Alcohols
Wang, Jie,Do, Dong-Minh,Chuah, Gaik-Khuan,Jaenicke, Stephan
, p. 247 - 254 (2013)
Beta-Silicalite-1 core-shell microcomposites with controllable shell thickness were synthesized and used as racemization catalysts in the one-pot dynamic kinetic resolution (DKR) of secondary alcohols by using lipase-catalyzed transesterification. The inert Silicalite-1 shell covered the external acidic sites of the Beta zeolite core, suppressing dehydration and non-enantioselective transesterification of the alcohol. The alcohols could penetrate the Silicalite-1 shell to access the acidic sites at the core Beta for racemization, however, the enzymatically formed (R)-esters were excluded owing to their larger size. As a result, the high ee of the (R)-ester products was conserved and dehydration side products were minimized. Owing to the shape selective nature of the composite racemization catalyst, small and readily available acyl donors could be used in the enzyme-catalyzed transesterification to obtain the esters with high enantiopurity. The DKR of 1-phenylethanol with isopropenyl acetate using an optimized core-shell catalyst, CS-60, gave 92% selectivity to ester formation and the desired (R)-1-phenylethyl acetate was formed with 94% ee.
Catalytic enantioselective addition of alkyl grignard reagents to aliphatic aldehydes
Fernandez-Mateos, Emilio,Macia, Beatriz,Yus, Miguel
, p. 1249 - 1254 (2013/06/27)
Herein, we report an efficient catalytic system for the enantioselective addition of alkyl Grignard reagents to a broad range of aliphatic aldehydes with good yields and enantioselectivities. Remarkably, the challenging methylmagnesium bromide (MeMgBr) can also be added to a variety of aliphatic aldehydes, providing versatile chiral methyl carbinol units with unprecedented yields and enantioselectivities in a simple one-pot procedure under mild conditions. Copyright
Highly enantioselective Rh-catalysed hydrogenation of 1-alkyl vinyl esters using phosphine-phosphoramidite ligands
Konrad, Tina Maria,Schmitz, Pascal,Leitner, Walter,Francio, Giancarlo
supporting information, p. 13299 - 13303 (2013/10/08)
MatPhos, a good mate for hard tasks: The asymmetric hydrogenation of 1-alkyl vinyl esters, thwarted so far by mediocre ee values and low activities, can now be achieved with MatPhos/Rh catalysts with ee values of 96-99 % for a variety of substrates at low catalyst loadings (0.1-1 mol %) and under mild conditions (5-20 bar H2, room temperature). After hydrolysis, the corresponding chiral secondary alkyl alcohols can be obtained in high enantiopurities providing a general and practical route to this important product class. Copyright