874955-58-5Relevant academic research and scientific papers
Enzymatic preparation of (1S,2R)- and (1R,2S)-stereoisomers of 2-halocycloalkanols
Kolodiazhna, Olga O.,Kolodiazhna, Anastasy O.,Kolodiazhnyi, Oleg I.
, p. 37 - 42 (2013/02/25)
The stereoisomers of cis-2-halocycloalkanols were resolved by a kinetically controlled transesterification with vinyl acetate in the presence of lipases in organic media. High enantioselectivities (ee >98%) and good isolated yields were obtained for all substrates using the appropriate lipase. Burkholderia cepacia lipase was the most efficient enzyme for the resolution of these substrates. The enantiomeric purities of the compounds were defined by derivatization with Mosher's acid and the absolute configurations were determined by chemical correlation.
Enantioselective synthesis of vicinal halohydrins via dynamic kinetic resolution
Ros, Abel,Magriz, Antonio,Dietrich, Hansjoerg,Fernandez, Rosario,Alvarez, Eleuterio,Lassaletta, Jose M.
, p. 127 - 130 (2007/10/03)
(Chemical Equation Presented) Expanding the scope of enantioselective catalysis via DKR, transfer hydrogenation of a variety of cyclic α-halo ketones was accomplished using the Noyori/Ikariya (R,R)- or (S,S)-I catalysts and either HCO2H/Et3N or HCO2Na/n-Bu 4NBr in H2O/CH2Cl2 as the hydrogen sources. Good yields of vicinal bromo-, chloro-, and fluorohydrins with excellent de and ee levels were achieved in most cases after a simple tuning of reaction conditions.
Organocatalytic asymmetric α-bromination of aldehydes and ketones
Bertelsen, Soren,Halland, Nis,Bachmann, Stephan,Marigo, Mauro,Braunton, Alan,Jorgensen, Karl Anker
, p. 4821 - 4823 (2008/01/27)
The first organocatalytic enantioselective α-bromination of aldehydes and ketones is presented; a C2-symmetric diphenylpyrrolidine catalyst afforded the α-brominated aldehydes in good yields and up to 96% ee, while ketones were α-brominated by
