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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

Puni tekst: engleski, pdf (6 MB) str. 701-718 preuzimanja: 318* citiraj
APA 6th Edition
Rusman, S., Kojić-Prodić, B., Ružić- Toroš, Ž., Šunjić, V. i Lenstra, A.T.H. (1990). Enantioselective Reduction of Some Aromatic Ketones by Baker's Yeast. Croatica Chemica Acta, 63 (4), 701-718. Preuzeto s https://hrcak.srce.hr/176529
MLA 8th Edition
Rusman, Snježana, et al. "Enantioselective Reduction of Some Aromatic Ketones by Baker's Yeast." Croatica Chemica Acta, vol. 63, br. 4, 1990, str. 701-718. https://hrcak.srce.hr/176529. Citirano 27.02.2021.
Chicago 17th Edition
Rusman, Snježana, Biserka Kojić-Prodić, Živa Ružić- Toroš, Vitomir Šunjić i Albert T. H. Lenstra. "Enantioselective Reduction of Some Aromatic Ketones by Baker's Yeast." Croatica Chemica Acta 63, br. 4 (1990): 701-718. https://hrcak.srce.hr/176529
Harvard
Rusman, S., et al. (1990). 'Enantioselective Reduction of Some Aromatic Ketones by Baker's Yeast', Croatica Chemica Acta, 63(4), str. 701-718. Preuzeto s: https://hrcak.srce.hr/176529 (Datum pristupa: 27.02.2021.)
Vancouver
Rusman S, Kojić-Prodić B, Ružić- Toroš Ž, Šunjić V, Lenstra ATH. Enantioselective Reduction of Some Aromatic Ketones by Baker's Yeast. Croatica Chemica Acta [Internet]. 1990 [pristupljeno 27.02.2021.];63(4):701-718. Dostupno na: https://hrcak.srce.hr/176529
IEEE
S. Rusman, B. Kojić-Prodić, Ž. Ružić- Toroš, V. Šunjić i A.T.H. Lenstra, "Enantioselective Reduction of Some Aromatic Ketones by Baker's Yeast", Croatica Chemica Acta, vol.63, br. 4, str. 701-718, 1990. [Online]. Dostupno na: https://hrcak.srce.hr/176529. [Citirano: 27.02.2021.]

Sažetak
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.

Hrčak ID: 176529

URI
https://hrcak.srce.hr/176529

Posjeta: 394 *