21087-76-3Relevant academic research and scientific papers
Study of the enantioselectivity of the CAL-B-catalysed transesterification of α-substituted α-propylmethanols and α-substituted benzyl alcohols
Garcia-Urdiales, Eduardo,Rebolledo, Francisca,Gotor, Vicente
, p. 3047 - 3052 (2001)
A study of the enantioselectivity exhibited by the lipase B from Candida antarctica in the transesterification of different α-substituted α-propylmethanols with vinyl acetate is shown. The best results are obtained when the large-sized (L) substituent of the alcohol is either a phenyl group or more especially a cyclohexyl group, although the reaction rates are lower than when linear or slightly branched groups are present. It is also found that ramification at the β-position of the L substituent has a deleterious effect on both lipase activity and enantioselectivity. Moreover, some α-substituted benzyl alcohols bearing medium-sized (M) substituents larger than an ethyl and smaller than a propyl group are resolved by means of this methodology with moderate-good enantioselectivities (E=46-57) and similar reaction rates.
A new facile chemoenzymatic synthesis of levamisole
Kamal, Ahmed,Khanna, G.B. Ramesh,Krishnaji,Ramu
, p. 613 - 615 (2007/10/03)
An efficient and facile chemoenzymatic synthesis of levamisole by employing lipase-mediated resolution of 3-hydroxy-3-phenylpropanenitrile followed by its conversion to β-amino alcohol as the key intermediate is described.
Efficient Lipase-Catalyzed Kinetic Resolution and Dynamic Kinetic Resolution of β-Hydroxy Nitriles. A Route to Useful Precursors for γ-Amino Alcohols
Pàmies, Oscar,B?ckvall, Jan-E.
, p. 726 - 731 (2007/10/03)
An efficient kinetic resolution of racemic β-hydroxy nitriles 1 was performed via Candida antarctica lipase (N-435)-catalyzed transesterification. A variety of racemic alkyl, aryl, and aryloxymethyl substituted β-hydroxy nitriles was efficiently transformed to the corresponding enantiomerically pure acetates (ee > 99% and conversion = 50%) with E values from 40 to > 1000. The combination of the enzymatic kinetic resolution with a ruthenium-catalyzed alcohol racemization led to a dynamic kinetic resolution (ee's up to 99%, yields up to 85%).
