Lipase-assisted preparation of enantiopure ferrocenyl sulfides possessing planar chirality and their use in the synthesis of chiral sulfoxides

Patti, Angela; Lambusta, Daniela; Piattelli, Mario; Nicolosi, Giovanni; McArdle, Patrick; Cunningham, Desmond; Walsh, M.A.

doi:10.1016/s0040-4020(96)01048-4

Cited by 30 publications

(9 citation statements)

References 14 publications

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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%

Dynamic kinetic resolution: synthesis of optically active α-amino acid derivatives

Brown

Parker

Turner

2000

Tetrahedron: Asymmetry

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Section: Scheme 12supporting

confidence: 53%

Dynamic kinetic resolution: synthesis of optically active α-amino acid derivatives

Brown

Parker

Turner

2000

Tetrahedron: Asymmetry

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“…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%

Comparative HPLC enantioseparation of ferrocenylalcohols on two cellulose‐based chiral stationary phases

2007

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The direct HPLC enantiomeric separation of several ferrocenylalcohols on the commercially available Chiralcel OD and Chiralcel OJ columns has been evaluated in normal-phase mode. Almost all the compounds were resolved on one or both chiral stationary phases (CSPs) with separation factor (alpha) ranging from 1.06 to 2.88 while the resolution (R(s)) varied from 0.63 to 12.70 In the separation of the alpha-ferrocenylalcohols 1a-e and the phenyl analogues 2a-e, which were all resolved except 1c, a similar trend in the retention behavior for the two series of alcohols was evidenced and the selectivity was roughly complementary on the two investigated CSP. For three ferrocenylacohols, chosen as model compounds, the influence of the mobile phase composition and temperature on the enantioseparation were investigated and additional information on the chiral recognition mechanism were deduced from the chromatographic behavior of their acetylderivatives.

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“…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%

Enzymatic approaches for the preparation of optically active non-centrochiral compounds

2016

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Lipase-assisted preparation of enantiopure ferrocenyl sulfides possessing planar chirality and their use in the synthesis of chiral sulfoxides

Cited by 30 publications

References 14 publications

Dynamic kinetic resolution: synthesis of optically active α-amino acid derivatives

Dynamic kinetic resolution: synthesis of optically active α-amino acid derivatives

Comparative HPLC enantioseparation of ferrocenylalcohols on two cellulose‐based chiral stationary phases

Enzymatic approaches for the preparation of optically active non-centrochiral compounds

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