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(E)-2-oxo-4(pyridin-3-yl)-3-but-3-enoic acid
(E)-3-(pyridine-3-yl)acrylaldehyde
-
-
-
?
(R)-benzoin
benzaldehyde + benzaldehyde
2 1H-indazole-6-carbaldehyde
(2R)-2-hydroxy-1,2-di(1H-indazol-6-yl)ethan-1-one
2 1H-pyrrole-2-carbaldehyde
(2R)-2-hydroxy-1,2-di(1H-pyrrol-2-yl)ethan-1-one
2 2-furaldehyde
(R)-2,2'-furoin
2 3-hydroxy-4-methoxybenzaldehyde
(2R)-2-hydroxy-1,2-bis(3-hydroxy-4-methoxyphenyl)ethan-1-one
2 4-formylbenzonitrile
4,4'-[(1R)-1-hydroxy-2-oxoethane-1,2-diyl]dibenzonitrile
2 4-hydroxy-3-methoxybenzaldehyde
(2R)-2-hydroxy-1,2-bis(4-hydroxy-3-methoxyphenyl)ethan-1-one
2 4-hydroxybenzaldehyde
(2R)-2-hydroxy-1,2-bis(4-hydroxyphenyl)ethan-1-one
2 4-nitrobenzaldehyde
(2R)-2-hydroxy-1,2-bis(4-nitrophenyl)ethan-1-one
2 benzaldehyde
2-hydroxy-1,2-diphenylethanone
95% conversion
-
-
?
2 butyraldehyde
(R)-5-hydroxy-4-octanone
96% conversion
-
-
?
2 naphthalene-2-carbaldehyde
(2R)-2-hydroxy-1,2-di(naphthalen-2-yl)ethan-1-one
2 phenanthrene-9-carbaldehyde
(2R)-2-hydroxy-1,2-di(phenanthren-9-yl)ethan-1-one
2 pyridine-3-carbaldehyde
(2R)-2-hydroxy-1,2-di(pyridin-3-yl)ethan-1-one
2 valeraldehyde
(R)-6-hydroxy-5-decanone
98% conversion
-
-
?
2,2'-[propane-1,3-diylbis(oxy)]bis(3-chlorobenzaldehyde)
(15R)-4,10-dichloro-15-hydroxy-7,8-dihydro-6H-dibenzo[f,j][1,5]dioxacycloundecin-14(15H)-one
-
50% conversion
-
-
?
2,2'-[propane-1,3-diylbis(oxy)]bis(3-methoxybenzaldehyde)
(15R)-15-hydroxy-4,10-dimethoxy-7,8-dihydro-6H-dibenzo[f,j][1,5]dioxacycloundecin-14(15H)-one
-
72% conversion
-
-
?
2,2'-[propane-1,3-diylbis(oxy)]bis(5-methoxybenzaldehyde)
(15R)-15-hydroxy-2,12-dimethoxy-7,8-dihydro-6H-dibenzo[f,j][1,5]dioxacycloundecin-14(15H)-one
-
89% conversion
-
-
?
2,2'-[propane-1,3-diylbis(oxy)]dibenzaldehyde
(15S)-15-hydroxy-7,8-dihydro-6H-dibenzo[f,j][1,5]dioxacycloundecin-14(15H)-one
-
-
-
-
?
2-furaldehyde
(R)-furoin
75% conversion
-
-
?
2-furaldehyde + 2,2-dimethoxyacetaldehyde
(2R)-1-(furan-2-yl)-2-hydroxy-3,3-dimethoxypropan-1-one
2-furaldehyde + 2-furaldehyde
(R)-2,2'-furoin
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-
i.e. (R)-1,2-di(furan-2-yl)-2-hydroxyketone
-
?
2-furaldehyde + 2-furaldehyde
2,2'-furoin
-
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r
2-hydroxy-1,2-diphenylethanone
2 benzaldehyde
2-hydroxy-1,2-diphenylethanone
benzaldehyde
2-hydroxypropiophenone
?
-
-
-
-
?
2-[3-(2-formylphenoxy)propoxy]pyridine-3-carbaldehyde
(14R)-14-hydroxy-7,8-dihydro-6H-[1,5]benzodioxacycloundecino[6,7-b]pyridin-15(14H)-one + (15R)-15-hydroxy-7,8-dihydro-6H-[1,5]benzodioxacycloundecino[6,7-b]pyridin-14(15H)-one
-
99% conversion
-
-
?
3,3'-[butane-1,4-diylbis(oxy)]dibenzaldehyde
3-(4-[3-[[3-[4-(4-formylphenoxy)butoxy]phenyl](hydroxy)acetyl]phenoxy]butoxy)benzaldehyde
-
-
-
-
?
3,3'-[propane-1,3-diylbis(oxy)]dibenzaldehyde
3-(3-[3-[[3-[3-(4-formylphenoxy)propoxy]phenyl](hydroxy)acetyl]phenoxy]propoxy)benzaldehyde
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-
-
-
?
3,5-dimethoxy-benzaldehyde
(R)-3,3',5,5'-tetramethoxy-benzoin
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-
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?
3,5-dimethoxy-benzaldehyde + 3,5-dimethoxy-benzaldehyde
(R)-3,3',5,5'-tetramethoxy-benzoin
-
-
-
-
?
3,5-dimethoxybenzaldehyde + 3,5-dimethoxybenzaldehyde
3,3',5,5'-tetramethoxybenzoin
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-
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-
r
3-chlorobenzaldehyde + acetaldehyde
(R)-(3-chlorophenyl)-2-hydroxy-1-propanone
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-
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-
r
3-ethoxybenzaldehyde
(R)-1,2-di(3-ethoxyphenyl)-2-hydroxyethanone
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-
-
-
?
3-methoxybenzaldehyde
(R)-3,3'-dimethoxybenzoin
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-
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-
r
3-methoxybenzaldehyde + 2-chlorobenzaldehyde
(R)-3-methoxy-2'-chlorobenzoin
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-
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-
r
3-methylbenzaldehyde
(R)-2-hydroxy-1,2-di(3-tolyl)-ethanone
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-
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?
4-ethoxybenzaldehyde
(R)-1,2-di(4-ethoxyphenyl)-2-hydroxyethanone
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?
4-methoxybenzaldehyde
(R)-1,2-di-(4-methoxy-phenyl)-2-hydroxy-ethan-1-one
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?
4-nitrobenzaldehyde + 2,2-dimethoxyacetaldehyde
(2R)-2-hydroxy-3,3-dimethoxy-1-(4-nitrophenyl)propan-1-one
-
-
-
-
?
5-bromo-2-[3-(2-formylphenoxy)propoxy]benzaldehyde
(15R)-12-bromo-15-hydroxy-7,8-dihydro-6H-dibenzo[f,j][1,5]dioxacycloundecin-14(15H)-one + (15R)-2-bromo-15-hydroxy-7,8-dihydro-6H-dibenzo[f,j][1,5]dioxacycloundecin-14(15H)-one
-
35% conversion
-
-
?
5-chloro-2-[3-(2-formylphenoxy)propoxy]benzaldehyde
(15R)-12-chloro-15-hydroxy-7,8-dihydro-6H-dibenzo[f,j][1,5]dioxacycloundecin-14(15H)-one + (15R)-2-chloro-15-hydroxy-7,8-dihydro-6H-dibenzo[f,j][1,5]dioxacycloundecin-14(15H)-one
-
72% conversion
-
-
?
acetaldehyde
(R)-acetoin
-
-
-
-
?
acetaldehyde + 3-chlorobenzaldehyde
(R)-1-(3-chloro-phenyl)-2-hydroxy-propan-1-one
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-
r
anisoin
4-methoxybenzaldehyde + 4-methoxybenzaldehyde
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-
?
benzaldehyde + (R)-2,2-dimethyl-1,3-dioxolan-4-carbaldehyde
acyloin + benzoin
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-
-
-
?
benzaldehyde + 2,2-dimethoxyacetaldehyde
(2R)-2-hydroxy-3,3-dimethoxy-1-phenylpropan-1-one
benzaldehyde + 2,2-dimethoxyacetaldehyde
3,3-dimethoxy-2-hydroxy-1-phenyl-propanone
-
-
-
-
?
benzaldehyde + 2-methylbutanal
(2R,3S)-2-hydroxy-3-methyl-1-phenylpentan-1-one + 1-hydroxy-3-methyl-1-phenylpentan-2-one
-
63% (2R,3S)-2-hydroxy-3-methyl-1-phenylpentan-1-one, 85% syn product, plus 37% 1-hydroxy-3-methyl-1-phenylpentan-2-one, 40% syn product
-
?
benzaldehyde + 2-methylpentanal
(2R,3S)-2-hydroxy-3-methyl-1-phenylhexan-1-one + 1-hydroxy-3-methyl-1-phenylhexan-2-one
-
50% (2R,3S)-2-hydroxy-3-methyl-1-phenylhexan-1-one, more than 99% syn poduct, plus 50% 1-hydroxy-3-methyl-1-phenylhexan-2-one
-
?
benzaldehyde + 2-methylpropanal
(2R)-2-hydroxy-3-methyl-1-phenylbutan-1-one + 1-hydroxy-3-methyl-1-phenylbutan-2-one
-
50% (2R)-2-hydroxy-3-methyl-1-phenylbutan-1-one, more than 99% enantiomeric excess, plus 50% 1-hydroxy-3-methyl-1-phenylbutan-2-one, 93% enantiomeric excess
-
?
benzaldehyde + acetaldehyde
(R)-2-hydroxy-1-phenyl-propanone
benzaldehyde + acetaldehyde
(R)-2-hydroxy-1-phenylpropanone
benzaldehyde + acetaldehyde
2-hydroxy-1-phenylpropanone
-
-
-
-
?
benzaldehyde + benzaldehyde
(R)-benzoin
-
immobilized BAL mediated reaction, conversion is low
i.e. 2-hydroxy-1,2-diphenylethan-1-one
-
?
benzaldehyde + benzaldehyde
benzoin
-
-
-
-
?
benzaldehyde + dimethoxy acetaldehyde
(R)-2-hydroxy-3,3-dimethoxy-1-phenylpropane-1-one
-
-
-
-
?
benzaldehyde + methoxy acetaldehyde
(R)-2-hydroxy-3-methoxy-1-phenylpropane-1-one
-
-
-
-
?
benzofuran-2-carbaldehyde
(R)-1,2-di(benzo-furan-2-yl)-2-hydroxyethanone
-
-
-
-
?
benzoin
benzaldehyde + benzaldehyde
Benzoylformate
?
-
-
-
-
?
benzoylformic acid
?
-
-
-
?
cyclohexylaldehyde + acetaldehyde
1-cyclohexyl 2-hydroxypropanone
-
-
-
-
?
dimethoxy acetaldehyde + benzaldehyde
(R)-2-hydroxy-3,3-dimethoxy-1-phenyl-propan-1-one
-
-
-
-
?
furan-2-aldehyde + 2,2-dimethoxyacetaldehyde
3,3-dimethoxy-2-hydroxy-1-furan-2-yl-propanone
-
-
-
-
?
furan-3-carbaldehyde
(R)-1,2-di(3-furanyl)-2-hydroxyethanone
-
-
-
-
?
furan-3-carbaldehyde + furan-3-carbaldehyde
(R)-1,2-di(3-furanyl)-2-hydroxyethanone
-
-
-
-
?
furan-carbaldehyde
(R)-1,2-difuryl-2-hydroxy-ethan-1-one
-
-
-
-
?
isovaleraldehyde
(R)-5-hydroxy-2,7-dimethyloctan-4-one
-
-
-
-
?
methoxy acetaldehyde + 4-methoxybenzaldehyde
(R)-2-hydroxy-3-methoxy-1-(4-methoxy-phenyl)-propan-1-one
-
-
-
-
r
methyl benzoylphosphonate
?
-
-
-
-
?
n-butanal
(R)-5-hydroxyoctan-4-one
-
-
-
-
?
n-pentanal
(R)-6-hydroxydecan-5-one
-
-
-
-
?
naphthalene-2-carbaldehyde + 2,2-dimethoxyacetaldehyde
(2R)-2-hydroxy-3,3-dimethoxy-1-(naphthalen-2-yl)propan-1-one
p-anisaldehyde + dimethoxy acetaldehyde
(R)-2-hydroxy-3,3-dimethoxy-1-(4-methoxyphenyl)propan-1-one
-
immobilized BAL mediated reaction
-
-
?
phenylpyruvic acid
?
-
-
-
?
propanal
4-hydroxyhexan-3-one
-
-
-
-
?
propanal + propanal
(S)-propioin
-
-
-
-
?
pyridine-3-carbaldehyde + 2,2-dimethoxyacetaldehyde
(2R)-2-hydroxy-3,3-dimethoxy-1-(pyridin-3-yl)propan-1-one
thiophene-3-carbaldehyde
(R)-2-hydroxy-1,2-di(3-thienyl)ethanone
-
-
-
-
?
additional information
?
-
(R)-benzoin

benzaldehyde + benzaldehyde
-
-
-
-
?
(R)-benzoin
benzaldehyde + benzaldehyde
-
-
-
-
r
2 1H-indazole-6-carbaldehyde

(2R)-2-hydroxy-1,2-di(1H-indazol-6-yl)ethan-1-one
-
-
-
?
2 1H-indazole-6-carbaldehyde
(2R)-2-hydroxy-1,2-di(1H-indazol-6-yl)ethan-1-one
-
-
-
-
?
2 1H-indazole-6-carbaldehyde
(2R)-2-hydroxy-1,2-di(1H-indazol-6-yl)ethan-1-one
-
-
-
-
?
2 1H-pyrrole-2-carbaldehyde

(2R)-2-hydroxy-1,2-di(1H-pyrrol-2-yl)ethan-1-one
-
-
-
?
2 1H-pyrrole-2-carbaldehyde
(2R)-2-hydroxy-1,2-di(1H-pyrrol-2-yl)ethan-1-one
-
-
-
-
?
2 1H-pyrrole-2-carbaldehyde
(2R)-2-hydroxy-1,2-di(1H-pyrrol-2-yl)ethan-1-one
-
-
-
-
?
2 2-furaldehyde

(R)-2,2'-furoin
-
-
-
?
2 2-furaldehyde
(R)-2,2'-furoin
-
-
-
-
?
2 2-furaldehyde
(R)-2,2'-furoin
-
-
-
-
?
2 3-hydroxy-4-methoxybenzaldehyde

(2R)-2-hydroxy-1,2-bis(3-hydroxy-4-methoxyphenyl)ethan-1-one
-
-
-
?
2 3-hydroxy-4-methoxybenzaldehyde
(2R)-2-hydroxy-1,2-bis(3-hydroxy-4-methoxyphenyl)ethan-1-one
-
-
-
-
?
2 3-hydroxy-4-methoxybenzaldehyde
(2R)-2-hydroxy-1,2-bis(3-hydroxy-4-methoxyphenyl)ethan-1-one
-
-
-
-
?
2 4-formylbenzonitrile

4,4'-[(1R)-1-hydroxy-2-oxoethane-1,2-diyl]dibenzonitrile
-
-
-
?
2 4-formylbenzonitrile
4,4'-[(1R)-1-hydroxy-2-oxoethane-1,2-diyl]dibenzonitrile
-
-
-
-
?
2 4-formylbenzonitrile
4,4'-[(1R)-1-hydroxy-2-oxoethane-1,2-diyl]dibenzonitrile
-
-
-
-
?
2 4-hydroxy-3-methoxybenzaldehyde

(2R)-2-hydroxy-1,2-bis(4-hydroxy-3-methoxyphenyl)ethan-1-one
-
-
-
?
2 4-hydroxy-3-methoxybenzaldehyde
(2R)-2-hydroxy-1,2-bis(4-hydroxy-3-methoxyphenyl)ethan-1-one
-
-
-
-
?
2 4-hydroxybenzaldehyde

(2R)-2-hydroxy-1,2-bis(4-hydroxyphenyl)ethan-1-one
-
-
-
?
2 4-hydroxybenzaldehyde
(2R)-2-hydroxy-1,2-bis(4-hydroxyphenyl)ethan-1-one
-
-
-
-
?
2 4-nitrobenzaldehyde

(2R)-2-hydroxy-1,2-bis(4-nitrophenyl)ethan-1-one
-
-
-
?
2 4-nitrobenzaldehyde
(2R)-2-hydroxy-1,2-bis(4-nitrophenyl)ethan-1-one
-
-
-
-
?
2 benzaldehyde

benzoin
-
-
-
?
2 benzaldehyde
benzoin
-
-
-
-
?
2 naphthalene-2-carbaldehyde

(2R)-2-hydroxy-1,2-di(naphthalen-2-yl)ethan-1-one
-
-
-
?
2 naphthalene-2-carbaldehyde
(2R)-2-hydroxy-1,2-di(naphthalen-2-yl)ethan-1-one
-
-
-
-
?
2 phenanthrene-9-carbaldehyde

(2R)-2-hydroxy-1,2-di(phenanthren-9-yl)ethan-1-one
-
-
-
?
2 phenanthrene-9-carbaldehyde
(2R)-2-hydroxy-1,2-di(phenanthren-9-yl)ethan-1-one
-
-
-
-
?
2 pyridine-3-carbaldehyde

(2R)-2-hydroxy-1,2-di(pyridin-3-yl)ethan-1-one
-
-
-
?
2 pyridine-3-carbaldehyde
(2R)-2-hydroxy-1,2-di(pyridin-3-yl)ethan-1-one
-
-
-
-
?
2-furaldehyde + 2,2-dimethoxyacetaldehyde

(2R)-1-(furan-2-yl)-2-hydroxy-3,3-dimethoxypropan-1-one
-
-
-
?
2-furaldehyde + 2,2-dimethoxyacetaldehyde
(2R)-1-(furan-2-yl)-2-hydroxy-3,3-dimethoxypropan-1-one
-
-
-
-
?
2-hydroxy-1,2-diphenylethanone

2 benzaldehyde
-
-
-
-
?
2-hydroxy-1,2-diphenylethanone
2 benzaldehyde
-
-
-
?
2-hydroxy-1,2-diphenylethanone
2 benzaldehyde
i.e. (R)-benzoin
-
-
r
2-hydroxy-1,2-diphenylethanone

benzaldehyde
-
-
-
-
r
2-hydroxy-1,2-diphenylethanone
benzaldehyde
-
-
-
-
r
2-hydroxy-1,2-diphenylethanone
benzaldehyde
-
-
-
r
benzaldehyde + 2,2-dimethoxyacetaldehyde

(2R)-2-hydroxy-3,3-dimethoxy-1-phenylpropan-1-one
-
-
-
?
benzaldehyde + 2,2-dimethoxyacetaldehyde
(2R)-2-hydroxy-3,3-dimethoxy-1-phenylpropan-1-one
-
-
-
-
?
benzaldehyde + acetaldehyde

(R)-2-hydroxy-1-phenyl-propanone
-
-
-
-
?
benzaldehyde + acetaldehyde
(R)-2-hydroxy-1-phenyl-propanone
-
-
-
-
?
benzaldehyde + acetaldehyde

(R)-2-hydroxy-1-phenylpropanone
-
-
-
-
?
benzaldehyde + acetaldehyde
(R)-2-hydroxy-1-phenylpropanone
-
-
-
-
r
benzoin

benzaldehyde + benzaldehyde
-
-
-
?
benzoin
benzaldehyde + benzaldehyde
-
-
-
-
?
benzoin
benzaldehyde + benzaldehyde
-
-
-
-
r
benzoin
benzaldehyde + benzaldehyde
-
the reaction is observed only in the liquid phase
-
-
r
benzoin
benzaldehyde + benzaldehyde
-
-
-
-
?
naphthalene-2-carbaldehyde + 2,2-dimethoxyacetaldehyde

(2R)-2-hydroxy-3,3-dimethoxy-1-(naphthalen-2-yl)propan-1-one
-
-
-
?
naphthalene-2-carbaldehyde + 2,2-dimethoxyacetaldehyde
(2R)-2-hydroxy-3,3-dimethoxy-1-(naphthalen-2-yl)propan-1-one
-
-
-
-
?
pyridine-3-carbaldehyde + 2,2-dimethoxyacetaldehyde

(2R)-2-hydroxy-3,3-dimethoxy-1-(pyridin-3-yl)propan-1-one
-
-
-
?
pyridine-3-carbaldehyde + 2,2-dimethoxyacetaldehyde
(2R)-2-hydroxy-3,3-dimethoxy-1-(pyridin-3-yl)propan-1-one
-
-
-
-
?
additional information

?
-
-
isobutyraldehyde, pivalaldehyde, and tert-butylacetaldehyde are no substrates
-
-
?
additional information
?
-
-
unable to cleave acetoin
-
-
?
additional information
?
-
-
shows no reaction with benzoylphosphonate
-
-
?
additional information
?
-
enzyme catalyzes the diastereoselective carboligation of aldehydes when benzaldehyde acts as the donor, and (+/-)-2-methyl-alkyl-aldehydes are used as acceptor substrates. When benzaldehyde is taken as an acceptor aldehyde, the diastereoselectivities obtained are poor in all cases tested
-
-
?
additional information
?
-
-
(R)-benzoin and acetaldehyde are converted in an immobilized BAL mediated reaction to 2-hydroxy-1,2-diphenylethan-1-one and (R)-2-hydroxy-1-phenylpropanone
-
-
?
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