Naslov
Preparation of S-2-Ethylhexyl-para-methoxycinnamate by Lipase Catalyzed Sequential Resolution

Autori
Majerić, Maja ; Šunjić, Vitomir

Izvornik
Tetrahedron: asymmetry (0957-4166) 7 (1996), 3; 815-824

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Enantioselectivity ; Hydrolysis

Sažetak
S-2-Ethylhexyl-para-methoxycinnamate S-6 is prepared by a sequential biocatalytic resolution. First, either enantioselective acetylation of rac 2-ethylhexanol (+/-)-1 by vinylacetate to R-(-)-2-ethylhexylacetate R-2, or alcoholysis of rac 2-ethylhexylbutyrate (+/-)-3 by n-butanol to S-(+)-2-ethylhexanol S-1 is completed, than, without isolation of the enantiomerically enreached S-alcohol, its enantioselective acylation with the activated para-methoxycinnammic acid derivatives 4, 5 is performed, both steps being catalyzed by different microbial lipases. The highest amplification of enantioselectivity is obtained by combining acetylation of rac 2-ethylhexanol catalyzed by Penicillium camembertii lipase or alcoholysis of rac 2-ethylhexylbutyrate catalyzed by Pseudomonas species lipase in the first step, with acylation of enantiomerically enriched S-1 by vinyl-para-methoxycinnamate 4 catalyzed by Lipozyme IM lipase ; 84.5% e.e. of S-6 is achieved in the first, and 88% e.e. in the second approach. Since the R-enantiomer of 2-ethylhexanol represents potential source of teratogenic R-2-ethylhexanoic acid, S-6 is regarded as biologicaly safer UV filter as compared to racemic 2-ethylhexyl-para-methoxycinnamate.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA