Direct asymmetric aldol reactions inspired by two types of natural aldolases : water-compatible organocatalysts and complexes

2012
journal article
article
72
dc.abstract.enIn this article the utility of water-compatible amino-acid-based catalysts was explored in the development of diastereo- and enantioselective direct aldol reactions of a broad range of substrates. Chiral $C_{2}$ -symmetrical proline- and valine- based amides and their $Zn^{II}$ complexes were designed for use as efficient and flexible chiral catalysts for enantioselective aldol reactions in water, on water, and in the presence of water. The presence of 5 mol % of the prolinamide-based catalyst affords asymmetric intermolecular aldol reactions between unmodified ketones and various aldehydes to give anti products with excellent enantioselectivities. We also demon- strate aldol reactions of more demanding substrates with high affinity to water (i.e., acetone and formaldehyde). Newly designed serine-based organocatalyst promoted aldol reaction of hydroxyacetone leading to syn -diols. For presented catalytic systems organic solvent-free conditions are also acceptable, making the elaborated methodology interesting from a green chemistry perspectives.pl
dc.affiliationWydział Chemii : Zakład Chemii Organicznejpl
dc.contributor.authorParadowska, Joannapl
dc.contributor.authorPasternak-Suder, Monika - 126154 pl
dc.contributor.authorGut, Bartosz - 106417 pl
dc.contributor.authorGryzło, Beatapl
dc.contributor.authorMłynarski, Jacek - 173385 pl
dc.date.accessioned2015-09-10T12:06:17Z
dc.date.available2015-09-10T12:06:17Z
dc.date.issued2012pl
dc.description.number1pl
dc.description.physical173-187pl
dc.description.points35pl
dc.description.volume77pl
dc.identifier.doi10.1021/jo201584wpl
dc.identifier.eissn1520-6904pl
dc.identifier.issn0022-3263pl
dc.identifier.urihttp://ruj.uj.edu.pl/xmlui/handle/item/15530
dc.languageengpl
dc.language.containerengpl
dc.rightsDodaję tylko opis bibliograficzny*
dc.rights.licencebez licencji
dc.rights.uri*
dc.subtypeArticlepl
dc.titleDirect asymmetric aldol reactions inspired by two types of natural aldolases : water-compatible organocatalysts and $Zn^{II}$ complexespl
dc.title.journalThe Journal of Organic Chemistrypl
dc.typeJournalArticlepl
dspace.entity.typePublication
dc.abstract.enpl
In this article the utility of water-compatible amino-acid-based catalysts was explored in the development of diastereo- and enantioselective direct aldol reactions of a broad range of substrates. Chiral $C_{2}$ -symmetrical proline- and valine- based amides and their $Zn^{II}$ complexes were designed for use as efficient and flexible chiral catalysts for enantioselective aldol reactions in water, on water, and in the presence of water. The presence of 5 mol % of the prolinamide-based catalyst affords asymmetric intermolecular aldol reactions between unmodified ketones and various aldehydes to give anti products with excellent enantioselectivities. We also demon- strate aldol reactions of more demanding substrates with high affinity to water (i.e., acetone and formaldehyde). Newly designed serine-based organocatalyst promoted aldol reaction of hydroxyacetone leading to syn -diols. For presented catalytic systems organic solvent-free conditions are also acceptable, making the elaborated methodology interesting from a green chemistry perspectives.
dc.affiliationpl
Wydział Chemii : Zakład Chemii Organicznej
dc.contributor.authorpl
Paradowska, Joanna
dc.contributor.authorpl
Pasternak-Suder, Monika - 126154
dc.contributor.authorpl
Gut, Bartosz - 106417
dc.contributor.authorpl
Gryzło, Beata
dc.contributor.authorpl
Młynarski, Jacek - 173385
dc.date.accessioned
2015-09-10T12:06:17Z
dc.date.available
2015-09-10T12:06:17Z
dc.date.issuedpl
2012
dc.description.numberpl
1
dc.description.physicalpl
173-187
dc.description.pointspl
35
dc.description.volumepl
77
dc.identifier.doipl
10.1021/jo201584w
dc.identifier.eissnpl
1520-6904
dc.identifier.issnpl
0022-3263
dc.identifier.uri
http://ruj.uj.edu.pl/xmlui/handle/item/15530
dc.languagepl
eng
dc.language.containerpl
eng
dc.rights*
Dodaję tylko opis bibliograficzny
dc.rights.licence
bez licencji
dc.rights.uri*
dc.subtypepl
Article
dc.titlepl
Direct asymmetric aldol reactions inspired by two types of natural aldolases : water-compatible organocatalysts and $Zn^{II}$ complexes
dc.title.journalpl
The Journal of Organic Chemistry
dc.typepl
JournalArticle
dspace.entity.type
Publication

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