Kinetic resolution of primary alcohols having remote stereogenic centers: lipase mediated kinetic resolution of (±)-3-chloro-3-arylpropanols

Isleyen, Alper; Tanyeli, Cihangir; Doğan, Özdemir

doi:10.1016/j.tetasy.2006.06.001

Cited by 14 publications

(12 citation statements)

References 16 publications

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“…This observation is consistent with the higher reactivity and low enantioselectivity of lipases towards less hindered alcohol nucleophiles. 19 The diacetylation of diol 1 with lipases all showed moderate to high enantioselectivity (see Table 1). This result is consistent with many studies, in which secondary alcohols have been resolved by lipases successfully.…”

Section: Resolution Of Diol (±)-1mentioning

confidence: 99%

A route to enantiomerically pure 5-(2′-hydroxyethyl)cyclopent-2-en-1-ol and its absolute configuration by Mosher esters

Chen

Nagabandi

Smith

et al. 2009

Tetrahedron: Asymmetry

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Section: Resolution Of Diol (±)-1mentioning

confidence: 99%

A route to enantiomerically pure 5-(2′-hydroxyethyl)cyclopent-2-en-1-ol and its absolute configuration by Mosher esters

Chen

Nagabandi

Smith

et al. 2009

Tetrahedron: Asymmetry

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“…[32][33][34] Representative examples of lipases used for acyl transfer are lipase from P. cepacia (Amano PS), lipase-B from Candida antarctica (CAL-B), Candida rugosa (CRL), and P. fluorescens (PFL). [48][49][50][51][52][53][54][55][56][57][58][59] Several strategies have been attempted to overcome this, such as the use of chiral or sterically demanding acyl donors, 56,60 optimization of solvation conditions, 61 or through sequential resolutions. [48][49][50][51][52][53][54][55][56][57][58][59] Several strategies have been attempted to overcome this, such as the use of chiral or sterically demanding acyl donors, 56,60 optimization of solvation conditions, 61 or through sequential resolutions.…”

Section: Introductionmentioning

confidence: 99%

1‐Hydroxymethyl‐7‐oxabicyclo[2.2.1]hept‐2‐ene skeleton in enantiopure form through enzymatic kinetic resolution

Reddy

Manheri

2019

Chirality

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Lipase-catalysed enantioselective acetylation and deacetylation routes were investigated to prepare 1,5,6-trisubstituted 7-oxabicyclo[2.2.1]hept-2-ene skeleton in enantio-pure form. The racemic alcohol (6) used in acetylation reaction was accessed through Diels-Alder reaction of TBDMS-protected furfuryl alcohol with maleic anhydride, followed by reduction-benzylation-desilylation sequence. After systematic screening of lipases and solvents, Candida antarctica B on acrylic resin in pentane was identified as the best system that gave >98% ee towards the (+) acetate with 40% conversion, in 30 minutes. Absolute stereochemistry of this product was confirmed by X-ray diffraction analysis of its 3,5-dinitrobenzoate derivative (9). Enantioselective deacetylation of the racemic acetate of this starting material was then studied with the same set of lipases. After various optimization studies, Candida antarctica B in toluene as the solvent was found to be the most effective that gave 49% conversion with >99% ee towards the (+)-alcohol (8) at the end of 18 hours.

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“…Several approaches to synthesize those molecules, including enantioenriched benzofused cycloalkane derivatives have been studied, mainly by metallic catalysis with Pd, 21,22 In, 23 Ru 24 and Cu. 31,32 In the sequential KR, when the first KR step leads to the product with only a moderate ee, the obtained product can be then submitted to a second KR step to achieve a highly enantioenriched product. Aiming enantiopure primary alcohols, we considered the application of kinetic resolution (KR) using lipases as biocatalysts.…”

Section: Introductionmentioning

confidence: 99%

Exploiting sequential lipase-catalyzed reactions to achieve enantiomerically pure chiral primary alcohols

et al. 2015

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The lipase-catalyzed enantioselective acetylation of benzofused cycloalkanescontaining primary alcohols with vinyl acetate was performed and allowed the isolation of enantiopure alcohols. Lipases from P. cepacea, C. rugosa, C. antarctica, P. fluorescens, C. cylindracea and M. meihei exhibited remarkable activity towards acetylation of these alcohols, affording the corresponding acetates with high conversion. Due to the high lipase activity toward primary alcohols, the enantioselectivity was low. To circumvent this problem, sequential kinetic resolution was employed with enantiocomplementary lipases leading to enantiomerically pure primary alcohols. This method represents a new approach to obtain chiral building blocks bearing ring systems, such as indanes, chromanes and tetralins. (6), 79 (6), 77 (11). 1 H NMR (300 MHz, CDCl 3 ) δ 7.25 -7.08 (m, 2H), 7.01 -6.74 (m, 2H), 6.85 (dd, J = 8.0 and 1.5 Hz, 1H), 4.39 (dd, J = 11.2 and 5.1 Hz, 1H), 4.32 -4.10 (m, 3H), 3.18 (hex, J = 3.2 Hz, 1H), 2.11 (s, 3H), 2.04 -1.86 (m, 1H), 0.99 -0.77 (m, 1H).

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Kinetic resolution of primary alcohols having remote stereogenic centers: lipase mediated kinetic resolution of (±)-3-chloro-3-arylpropanols

Cited by 14 publications

References 16 publications

A route to enantiomerically pure 5-(2′-hydroxyethyl)cyclopent-2-en-1-ol and its absolute configuration by Mosher esters

A route to enantiomerically pure 5-(2′-hydroxyethyl)cyclopent-2-en-1-ol and its absolute configuration by Mosher esters

1‐Hydroxymethyl‐7‐oxabicyclo[2.2.1]hept‐2‐ene skeleton in enantiopure form through enzymatic kinetic resolution

Exploiting sequential lipase-catalyzed reactions to achieve enantiomerically pure chiral primary alcohols

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