Candida Rugosa lipase-catalyzed kinetic resolution of β-hydroxy-β-arylpropionates and δ-hydroxy-δ-aryl-β-oxo-pentanoates

Xu, Chengfu; Yuan, Cai

doi:10.1016/j.tet.2004.12.059

Cited by 78 publications

(36 citation statements)

References 80 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As was mentioned, usually synthesis of the cyclohexanones of this type is carried out via one-pot MCRs, where several organic fragments are coupled in one step with a carbon-carbon formation and subsequent cyclization [5][6][7][8][10][11][12][13][14][15][16][17][18][19]. The methods of further modification of the thus prepared cyclohexanones with mono-or polyfunctional nucleophiles are also well studied [20][21][22][23][24][25][26][27][28].…”

Section: Introductionmentioning

confidence: 99%

Syntheses and some features of five new cyclohexane-1,3-dicarboxylates with multiple stereogenic centers

Ismiyev¹,

Maharramov²,

Aliyeva³

et al. 2013

Journal of Molecular Structure

View full text Add to dashboard Cite

Section: Introductionmentioning

confidence: 99%

Syntheses and some features of five new cyclohexane-1,3-dicarboxylates with multiple stereogenic centers

Ismiyev¹,

Maharramov²,

Aliyeva³

et al. 2013

Journal of Molecular Structure

View full text Add to dashboard Cite

“…The absolute configuration of this aldol adduct was determined to be R by comparison of its optical rotation with that in the literature. [16] The reaction is thought to proceed as follows: Diarylprolinol catalyst 1 reacts with acetaldehyde to generate enamine 5, which reacts with an electrophilic aldehyde as shown in Figure 2. This model can explain the absolute configuration of the aldol product.…”

mentioning

confidence: 99%

A Diarylprolinol in an Asymmetric, Catalytic, and Direct Crossed‐Aldol Reaction of Acetaldehyde

et al. 2008

View full text Add to dashboard Cite

No over‐reacting: A diarylprolinol was found to be an effective organocatalyst of the direct, enantioselective aldol reaction of acetaldehyde, affording β‐hydroxy α‐unsubstituted aldehydes in good yield with excellent enantioselectivity (see scheme). In the proposed transition state the aldehyde reacts on the more hindered face of the intermediate enamine as a consequence of the hydrogen bond between the aldehyde and the OH group of the organocatalyst.

show abstract

“…The preparation of the title compoundispossible in different ways.Methyl cinnamate was convertedwith methyl acetate in an ester condensation to yieldthe desiredcompound [5]. Furthermore it can be obtaineda sb y-product in lipase-catalysed reactions of b-hydroxy-b-arylpropionates [6] or through conversion of 3-oxo-5-phenyl-pent-4-enoic acidm ethyl ester with oxalate [7]. Otherwise,inthe multi-stepsynthesis of the natural product ABT-418 [8] the titlecompound was synthesized as an important intermediate.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of (2Z,4E)-3-hydroxy-5-phenyl-penta-2,4-dienonic acid methyl ester, (C6H5)(CH)2COH(CH)CO2CH3

Mamat¹,

Köckerling²,

Geers³

2008

Zeitschrift Für Kristallographie - New Crystal Structures

View full text Add to dashboard Cite

Source of materialThe title compound was found as asideproductinthe formation of the respective saturated derivative 3-oxo-5-phenyl-pentanoic acid methyl ester according to [1]. After purification via column chromatography as mall amounto fc olorlessn eedles was obtained from am ixture of both compounds after several weeks (m.p. 72°C). Analytical data are in accordance with the previously published data [2]. Experimental detailsHydrogen atoms were located from Fourier difference maps, and refined with isotropic displacement parameters based on the bondedatoms. Discussion 1,3-Dicarbonyl compounds are of substantial interest as dielectrophilic sources in the synthesis of various heterocyclic compounds [3,4]. The preparation of the title compoundispossible in different ways.Methyl cinnamate was convertedwith methyl acetate in an ester condensation to yieldthe desiredcompound [5]. Furthermore it can be obtaineda sb y-product in lipase-catalysed reactions of b-hydroxy-b-arylpropionates [6] or through conversion of 3-oxo-5-phenyl-pent-4-enoic acidm ethyl ester with oxalate [7]. Otherwise,inthe multi-stepsynthesis of the natural product ABT-418 [8] the titlecompound was synthesized as an important intermediate. The double bond in the title molecule adopts a trans configuration with at orsion angle of almost1 80°(178.09(1)°). The aromatic system, the double bonds and the carbonyl group at C11 form a conjugated p-system. Due to the conjugation with the carbonyl groups the double bond is activated, hence substrate addition follows in aregioselective manner. The lengthofthe bond C9=C10 (1.336(3) Å)isinthe range of typical C=Cdouble bonds. Otherwise, the C9-O3 distance (1.342(2) Å)corresponds to aC-O single bond. An intramolecular hydrogen bond is found between the OH group at C9 and the adjacent carboxyl group. In solution this compound shows keto-enol tautorism(20:80 ratio ratified by NMR measurement [2]).The refinementofthe occupation of the H3B siteshows, thatthe enolic form is preferred in the crystalline solid state.

show abstract

Candida Rugosa lipase-catalyzed kinetic resolution of β-hydroxy-β-arylpropionates and δ-hydroxy-δ-aryl-β-oxo-pentanoates

Cited by 78 publications

References 80 publications

Syntheses and some features of five new cyclohexane-1,3-dicarboxylates with multiple stereogenic centers

Syntheses and some features of five new cyclohexane-1,3-dicarboxylates with multiple stereogenic centers

A Diarylprolinol in an Asymmetric, Catalytic, and Direct Crossed‐Aldol Reaction of Acetaldehyde

Crystal structure of (2Z,4E)-3-hydroxy-5-phenyl-penta-2,4-dienonic acid methyl ester, (C6H5)(CH)2COH(CH)CO2CH3

Contact Info

Product

Resources

About