1997
DOI: 10.1016/s0040-4020(96)01048-4
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Lipase-assisted preparation of enantiopure ferrocenyl sulfides possessing planar chirality and their use in the synthesis of chiral sulfoxides

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Cited by 30 publications
(9 citation statements)
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“…Enzymatic ammoniolysis has also been employed in a one pot, double resolution process for the synthesis of fatty acid amides and carboxylic amides. 49 Table 3 •50- 54 The results lead to a preferred enantiomer model (with regard to the size of the ortho substituent to the hydroxymethyl group) similar to that proposed by Kazlauskas 19 for the enantiopreference of lipases in the recognition of secondary alcohols. Ferrocenes containing central chirality have also been resolved enzymatically.…”
Section: Scheme 12supporting
confidence: 53%
“…Enzymatic ammoniolysis has also been employed in a one pot, double resolution process for the synthesis of fatty acid amides and carboxylic amides. 49 Table 3 •50- 54 The results lead to a preferred enantiomer model (with regard to the size of the ortho substituent to the hydroxymethyl group) similar to that proposed by Kazlauskas 19 for the enantiopreference of lipases in the recognition of secondary alcohols. Ferrocenes containing central chirality have also been resolved enzymatically.…”
Section: Scheme 12supporting
confidence: 53%
“…Racemic ferrocenylalcohols were prepared according reported procedures, mainly based on the metalation of the ferrocene and subsequent quenching with the suitable electrophile 6 ; enantiomerically enriched samples were obtained by asymmetric reduction of the corresponding ketones, 19,20 by lipase-catalyzed enantioselective esterification of racemic alcohols [21][22][23] or synthesis with enantiopure reagents. The dead time (t 0 ) was obtained from the elution time of unretained 1,3,5-tri-iso-propylbenzene and mobile phase elution was made isocratically at flow 0.5 ml/min using n-hexane and 2-PrOH at different percentages (% v/v) as specified in Tables 1 and 2.…”
Section: Materials and Methods Chromatographic Conditionsmentioning
confidence: 99%
“…On the basis of Izumi's studies on simple 1,2-disubstituted ferrocene and ferrocenophane lipase substrates, 80,81 the group of Nicolosi performed an in-depth investigation on the kinetic resolution of 2-substituted ferrocenemethanols. 82,83,84,85 In the enzyme-mediated acetylation, the lipases of Candida antarctica (type B) and Candida cylindracea, respectively, provided moderate to good enantioselectivities for a variety of halogen-, sulfide-and aminomethyl-functionalized ferrocenes (scheme 37). Later, Aribi-Zouioueche and Riant published further refinements of this method (e.g.…”
Section: Scheme 36 Selective Hydrolysis Of Ferrocenophane 82mentioning
confidence: 99%