199383-77-2Relevant academic research and scientific papers
Chemoenzymatic synthesis of a non-peptide tachykinin NK-2 antagonist
Carnell, Andrew J.,Hernandez, Maria Luisa Escudero,Pettman, Alan,Bickley, Jamie F.
, p. 6929 - 6933 (2007/10/03)
The synthesis of a tachykinin NK-2 antagonist (S)-11 has been carried out in four steps starting from the the (S)-(+)-enol acetate 3, which was obtained in 100% e.e. by resolution of the racemic ester with Pseudomonas fluorescens lipase. The absolute configuration of the enol acetate (+)-3 was confirmed by X-ray analysis of the camphanyl derivative 13. (C) 2000 Elsevier Science Ltd.
Desymmetrisation of 4,4-disubstituted cyclohexanones by enzyme-catalysed resolution of their enol acetates
Allan, Graham,Carnell, Andrew J.,Hernandez, Maria Luisa Escudero,Pettman, Alan
, p. 3382 - 3388 (2007/10/03)
Enol acetates 3 10 derived from prochiral 4,4-disubstituted cyclohexanones can be resolved with Pseudomonas fiuorescens lipase to give enantiomerically pure (>99% ee) enol esters by transesterification with n-BuOH. The product ketones are prochiral and can easily be recycled giving an overall desymmetrisation of the ketone. Highest selectivity was obtained for substrates containing a 4-cyano and 4-aryl or a 4-benzyloxy substituent. The methodology was compared to asymmetric deprotonation-enolate trapping using the chiral base (S,S)-bis(α-methylbenzyl)amide which gave low (54-64%) ee's for this class of ketones.
Desymmetrisation of prochiral ketones by catalytic enantioselective hydrolysis of their enol esters using enzymes
Carnell, Andrew J.,Barkley, Jim,Singh, Amarjit
, p. 7781 - 7784 (2007/10/03)
Desymmetrisation of 4-cyano-4-phenylcyclohexanone 1 has been achieved by enzyme-catalysed enantioselective alcoholysis with n-butanol of the derived racemic enol acetate 2 in tetrahydrofuran. The absolute configuration of the enol aceate (-)-(S)-2 (100% e.e.) obtained was determined by X-ray analysis of the camphanyl derivative 7.
