Resolution of racemic sterically hindered secondary alcohols via enzymatic alcoholysis of their esters. The first enzymatic preparation of optically pure 2,2,2-trifluoro-1-(9-anthryl)ethanols

Shkolnik, Eleonora; Gutman, Arie L.

doi:10.1016/0968-0896(94)85003-8

Cited by 7 publications

(2 citation statements)

References 23 publications

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“…The same enzyme catalyzed the enantioselective alcoholysis of other trifluoro(aryl) ethanol chloroacetates [248] and in a previous paper the resolution of 2,2,2,trifluoro-1-(9-anthryl)ethanol butyrate with 1-butanol as deacylating agent and PPL as biocatalyst was reported [249]. Similarly, lipase AK is able to resolve with 1-propanol the acetate of racemic 2,2,2-trifluoro-1-(indole-3-) and (1pyrenyl)ethanol [250,251].…”

Section: Aromatic Compoundsmentioning

confidence: 75%

Lipase-Catalyzed Deacylation by Alcoholysis: A Selective, Useful Transesterification Reaction

Santaniello¹,

Casati²,

Ciuffreda

2006

COC

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Alcoholysis is a transesterification reaction, according to which an ester RCOOR′ reacts with an alcohol R′′OH with formation of another ester RCOOR′′ and liberation of the alcohol R′OH. The deacylation may be catalyzed by a lipase in organic solvents and constitutes a useful step in the synthesis of complex molecules where different groups are present. The enzymatic deprotection procedure acquires a particular significance, considering the hydrophobic nature of the substrates and their solubility in organic solvents. In these non-conventional media lipases are still considerably active and a great variety of examples of regio-and chemoselectivity of the enzymatic deacylation have been reported. Application of resolution or asymmetrization procedures to the preparation of stereochemically pure products will also be examined and discussed. O AcO AcO OAc O AcO AcO OH Lipase-Catalyzed Deacylation by Alchololysis

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Section: Aromatic Compoundsmentioning

confidence: 75%

Lipase-Catalyzed Deacylation by Alcoholysis: A Selective, Useful Transesterification Reaction

Santaniello¹,

Casati²,

Ciuffreda

2006

COC

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“…Only C. rugosa and P. cepacia indicated some selectivity (48-56% ee). However, the best results were obtained by carrying out the alcoholysis of the acetate derivative (Bevinakatti and Banerji, 1991;Shkolnik and Gutman, 1994) (5) in a diisopropyl ether/n-butanol (3:1) mixture employing P. cepacia lipase. The marked increase in enantiospecificity in changing the reaction conditions from acylation of 4 to alcoholysis of 5 could be due to steric reasons.…”

Section: Resultsmentioning

confidence: 99%

Chemoenzymatic Synthesis of Homochiral (R)- and (S)-Karahanaenol from (R)-Limonene

Roy

1999

J. Agric. Food Chem.

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Terpinolene oxide, a monoterpene belonging to the p-menthane group, is easily derived from naturally abundant (R)-limonene. It was isomerized with montmorillonite clay catalyst to karahanaenone (2,2, 5-trimethylcyclohept-4-en-1-one) by ring enlargement. The enantiomers of the corresponding alcohol, karahanaenol (2,2, 5-trimethylcyclohept-4-en-1- ol), known for their individual organoleptic properties, were resolved through Pseudomonas cepacia lipase mediated enantiospecific alcoholysis of its acetate derivative.

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Synthetic applications of enzymatic reactions in organic solvents

Gutman

Shapira

1995

Microbial and Eznymatic Bioproducts

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Resolution of racemic sterically hindered secondary alcohols via enzymatic alcoholysis of their esters. The first enzymatic preparation of optically pure 2,2,2-trifluoro-1-(9-anthryl)ethanols

Cited by 7 publications

References 23 publications

Lipase-Catalyzed Deacylation by Alcoholysis: A Selective, Useful Transesterification Reaction

Lipase-Catalyzed Deacylation by Alcoholysis: A Selective, Useful Transesterification Reaction

Chemoenzymatic Synthesis of Homochiral (R)- and (S)-Karahanaenol from (R)-Limonene

Synthetic applications of enzymatic reactions in organic solvents

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