Pregled bibliografske jedinice broj: 166046
Enantioselective Acetylation of Prochiral 2-(omega-Ferrocenylalkyl)propane-1, 3-diols
Enantioselective Acetylation of Prochiral 2-(omega-Ferrocenylalkyl)propane-1, 3-diols // 13th European Symposium on Organic Chemistry : ESOR-13 : abstracts ; (P1-41)
Zagreb, 2003. str. 168-168 (poster, nije recenziran, sažetak, znanstveni)
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Naslov
Enantioselective Acetylation of Prochiral 2-(omega-Ferrocenylalkyl)propane-1, 3-diols
Autori
Đaković, Senka ; Lapić, Jasmina ; Rapić, Vladimir
Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni
Izvornik
13th European Symposium on Organic Chemistry : ESOR-13 : abstracts ; (P1-41)
/ - Zagreb, 2003, 168-168
Skup
European Symposium on Organic Chemistry (13 ; 2003)
Mjesto i datum
Dubrovnik, Hrvatska; Cavtat, Hrvatska, 10.09.2003. - 15.09.2003
Vrsta sudjelovanja
Poster
Vrsta recenzije
Nije recenziran
Ključne riječi
prochiral 2-(omega-ferrocenylalkyl)propane-1; 3-diols; enantioselective acetylation; microbial lipases
(prochiral 2-(omega-ferrocenylalkyl)propane-1; 3- diols; enantioselective acetylation; microbial lipases)
Sažetak
Prochiral diols (meso-compounds or molecules possesing pseudo-asymmetric centers) are very useful synthetic intermediates because the maximum feasible yield upon their enzymatic transformation is not limited to 50 %, as happens when resolving racemic mixtures. Different prochiral ferrocene diols (1, 4 and 7), as well as the corresponding monoacetates (2, 5 and 8) and diacetates (3, 6 and 9) were prepared according to the procedure described in our previous paper1. Enantioselective acetylation (desymmetrization) of prochiral 2-(ferrocenylmethyl)propane-1, 2-diol (1), 2-(2-ferrocenylethyl)propane-1, 2-diol (4) and 2-(3-ferrocenylpropyl)propane-1, 2-diol (7) into chiral monoacetates [(+)-2, (+)-5, (+)-8], with a series of microbial lipases in benzene at 27 ?C, revealed the lipase from Pseudomonas species (PSL) as the most selective. Acetylation was fastest and most enantioselective for conversion 1?(+)-2 by PSL (97 % e.e.). By comparison of the compounds (+)-2, (+)-5, (+)-8 with their benzene analogues of the known (R) absolute configuration, on the basis of their eluation orders on Chiracel OD, and the same direction of their optical rotations, for (+)-monoacetates 2, 5 and 8 R-configuration could be proposed.
Izvorni jezik
Engleski
Znanstvena područja
Kemija
