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Achiral bis-imine in combination with CoCl?: A remarkable effect on enantioselectivity of lipase-mediated acetylation of racemic secondary alcohol.

ABSTRACT: A bis-imine (prepared via a new FeCl?-based method) in combination with CoCl? facilitated lipase-mediated acetylation of the (R)-isomer of a racemic benzylic secondary alcohol with 91% ee(s). The methodology was used for the preparation of the known drug rivastigmine.

SUBMITTER: Arunkumar K

PROVIDER: S-EPMC3002020 | biostudies-literature | 2010 Dec

REPOSITORIES: biostudies-literature

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Achiral bis-imine in combination with CoCl₂: A remarkable effect on enantioselectivity of lipase-mediated acetylation of racemic secondary alcohol.

Arunkumar K K Reddy M Appi MA Kumar T Sravan TS Kumar B Vijaya BV Chandrasekhar K B KB Kumar P Rajender PR Pal Manojit M

Beilstein journal of organic chemistry 20101210

A bis-imine (prepared via a new FeCl₃-based method) in combination with CoCl₂ facilitated lipase-mediated acetylation of the (R)-isomer of a racemic benzylic secondary alcohol with 91% ee(s). The methodology was used for the preparation of the known drug rivastigmine. ...[more]

PMID: 21160565

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Project description:Chiral molecular crystals built up by chiral molecules without inversion centers have attracted much interest owing to their versatile functionalities related to optical, magnetic, and electrical properties. However, there is a difficulty in chiral crystal growth due to the lack of symmetry. Therefore, we made the molecular design to introduce intermolecular hydrogen bonds in chiral crystals. Racemic and enantiopure bis(ethylenedithio)tetrathiafulvalene (BEDT-TTF) derivatives possessing hydroxymethyl groups as the source of hydrogen bonds were designed. The novel racemic trans-vic-(hydroxymethyl)(methyl)-BEDT-TTF 1, and racemic and enantiopure trans-vic-bis(hydroxymethyl)-BEDT-TTF 2 were synthesized. Moreover, the preparations, crystal structure analyses, and electrical resistivity measurements of the novel achiral charge transfer salt θ(21)-[(S,S)-2]3[(R,R)-2]3(ClO4)2 and the chiral salt α'-[(R,R)-2]ClO4(H2O) were carried out. In the former θ(21)-[(S,S)-2]3[(R,R)-2]3(ClO4)2, there are two sets of three crystallographically independent donor molecules [(S,S)-2]2[(R,R)-2] in a unit cell, where the two sets are related by an inversion center. The latter α'-[(R,R)-2]ClO4(H2O) is the chiral salt with included solvent H2O, which is not isostructural with the reported chiral salt α'-[(S,S)-2]ClO4 without H2O, but has a similar donor arrangement. According to the molecular design by introduction of hydroxy groups and a ClO4 (-) anion, many intermediate-strength intermolecular hydrogen bonds (2.6-3.0 Å) were observed in these crystals between electron donor molecules, anions, and included H2O solvent, which improve the crystallinity and facilitate the extraction of physical properties. Both salts are semiconductors with relatively low resistivities at room temperature and activation energies of 1.2 ohm cm with E a = 86 meV for θ(21)-[(S,S)-2]3[(R,R)-2]3(ClO4)2 and 0.6 ohm cm with E a = 140 meV for α'-[(R,R)-2]2ClO4(H2O), respectively. The variety of donor arrangements, θ(21) and two kinds of α'-types, and their electrical conductivities of charge transfer complexes based upon the racemic and enantiopure (S,S)-2, and (R,R)-2 donors originates not only from the chirality, but also the introduced intermolecular hydrogen bonds involving the hydroxymethyl groups, perchlorate anion, and the included solvent H2O.

Dataset Information

Achiral bis-imine in combination with CoCl?: A remarkable effect on enantioselectivity of lipase-mediated acetylation of racemic secondary alcohol.

Publications

Achiral bis-imine in combination with CoCl₂: A remarkable effect on enantioselectivity of lipase-mediated acetylation of racemic secondary alcohol.

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