Original scientific paper

Enantioselective Reduction of Some Aromatic Ketones by Baker's Yeast

Snježana Rusman ; "Ruđer Bošković" Institute, PiBox 1016, 41001 Zagreb, Croatia, Yugoslavia
Biserka Kojić-Prodić ; "Ruđer Bošković" Institute, PiBox 1016, 41001 Zagreb, Croatia, Yugoslavia
Živa Ružić- Toroš ; "Ruđer Bošković" Institute, PiBox 1016, 41001 Zagreb, Croatia, Yugoslavia
Vitomir Šunjić ; "Ruđer Bošković" Institute, PiBox 1016, 41001 Zagreb, Croatia, Yugoslavia
Albert T. H. Lenstra ; Universitaire Instelling Antwerpen, Universiteitsplein 1, B-2610 Wilrijk; Belgium

Abstract

The reduction of aromatic ketones 1- 6 by baker's yeast showed that acceptability of the substrates is not governed either by the number of aryl groups at by the distance of the carbonyl group from the aryl moiety. Relative rates of conversion of 3, 4, and 6 vs. ethyl acetoacetate as the "standard" substrate were reproducible
in the order 3>6>4. Strong inhibition of reduction of ethyl acetoacetate by benzene vanished at very law concentrations of both. Reduction of phenyl-pyrid- 2'yl-methyl ketone (1) and its deazaanalogue (6) gave the chiral sec. alcohols of the opposite configuration. (-) -7 and (+) -12, respectively. This could be ascribed to the prevalent binding of enol lA by the opposite enantioface, as compared lo 6. Absolute configuratian of ( - ) -7 is tentatively assigned as R by the empirical rule based on the lNMR spectra of Mosher's acid esters 13-15. This assignment is confirmed by the single crystal X-ray structure determination of camphanic acid ester 16A, which on hydrolysis affards (-) - 7.

Keywords

Hrčak ID:

176529

URI

https://hrcak.srce.hr/176529

Publication date:

26.3.1991.

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