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On the Way to α-Methyl-α-amino Acids; Unusual Elimination-addition in 3,3-Disubstituted 1,4-Benzodiazepin-2-ones and Inversion of Enantioselectivity in the Lipase Catalyzed Acetylation

Amir Avdagić ; Ruđer Bošković Institute, P. O. Box 180, Bijenička 54, HR-10002 Zagreb, Croatia
Vitomir Šunjić ; Ruđer Bošković Institute, P. O. Box 180, Bijenička 54, HR-10002 Zagreb, Croatia

Puni tekst: engleski, pdf (118 KB) str. 743-753 preuzimanja: 104* citiraj
APA 6th Edition
Avdagić, A. i Šunjić, V. (2000). On the Way to α-Methyl-α-amino Acids; Unusual Elimination-addition in 3,3-Disubstituted 1,4-Benzodiazepin-2-ones and Inversion of Enantioselectivity in the Lipase Catalyzed Acetylation. Croatica Chemica Acta, 73 (3), 743-753. Preuzeto s https://hrcak.srce.hr/132013
MLA 8th Edition
Avdagić, Amir i Vitomir Šunjić. "On the Way to α-Methyl-α-amino Acids; Unusual Elimination-addition in 3,3-Disubstituted 1,4-Benzodiazepin-2-ones and Inversion of Enantioselectivity in the Lipase Catalyzed Acetylation." Croatica Chemica Acta, vol. 73, br. 3, 2000, str. 743-753. https://hrcak.srce.hr/132013. Citirano 26.09.2020.
Chicago 17th Edition
Avdagić, Amir i Vitomir Šunjić. "On the Way to α-Methyl-α-amino Acids; Unusual Elimination-addition in 3,3-Disubstituted 1,4-Benzodiazepin-2-ones and Inversion of Enantioselectivity in the Lipase Catalyzed Acetylation." Croatica Chemica Acta 73, br. 3 (2000): 743-753. https://hrcak.srce.hr/132013
Harvard
Avdagić, A., i Šunjić, V. (2000). 'On the Way to α-Methyl-α-amino Acids; Unusual Elimination-addition in 3,3-Disubstituted 1,4-Benzodiazepin-2-ones and Inversion of Enantioselectivity in the Lipase Catalyzed Acetylation', Croatica Chemica Acta, 73(3), str. 743-753. Preuzeto s: https://hrcak.srce.hr/132013 (Datum pristupa: 26.09.2020.)
Vancouver
Avdagić A, Šunjić V. On the Way to α-Methyl-α-amino Acids; Unusual Elimination-addition in 3,3-Disubstituted 1,4-Benzodiazepin-2-ones and Inversion of Enantioselectivity in the Lipase Catalyzed Acetylation. Croatica Chemica Acta [Internet]. 2000 [pristupljeno 26.09.2020.];73(3):743-753. Dostupno na: https://hrcak.srce.hr/132013
IEEE
A. Avdagić i V. Šunjić, "On the Way to α-Methyl-α-amino Acids; Unusual Elimination-addition in 3,3-Disubstituted 1,4-Benzodiazepin-2-ones and Inversion of Enantioselectivity in the Lipase Catalyzed Acetylation", Croatica Chemica Acta, vol.73, br. 3, str. 743-753, 2000. [Online]. Dostupno na: https://hrcak.srce.hr/132013. [Citirano: 26.09.2020.]

Sažetak
(−)-3 -Methanesulfoxymethyl-3-acetoxoymethyl-7-chloro-5-phenyl-1,4-benzodiazepin-2-one, (−)-2, reacts with ethanethiol in the presence of a strong base affording racemic elimination-addition product 3-ethylthiomethyl-7-chloro-5-phenyl-1,4-benzodiazepin-2-one (4). In-termediary 3-methylene-7-chloro-5-phenyl-1,4-benzodiazepin-2-one (3) is formed by pericyclic C−C bond breaking during elimination of both acyloxy groups. The second approach to α-methyl-α-amino acids comprises kinetic resolution of racemic 3-hydroxymethyl-3-benzyl-7-chloro-5-phenyl-1,4-benzodiazepin-2-one (7) via acetylation by Novozym 435 lipase; enantiomeric excess (e.e.) for alcohol (3S)-(+)-7 33.2%; e.e. for acetate (3R)-(−)-8 30.2%. Opposite direction of enantio-selectivity during acetylation of 7 and the recently studied 9 (Ref. 3) was established by determination of absolute conformation and rela-tive configuration at C(3) (pseudoaxial/pseudoequatorial) by com-bining CD and 1H NMR spectroscopy.

Ključne riječi
1,4-Benzodiazepin-2-ones; kinetic resolution; absolute configuration

Hrčak ID: 132013

URI
https://hrcak.srce.hr/132013

Posjeta: 196 *