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Direct asymmetric aldol reactions inspired by two types of natural aldolases : water-compatible organocatalysts and
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
cris.lastimport.scopus | 2024-04-07T13:44:27Z | |
dc.abstract.en | 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. | pl |
dc.affiliation | Wydział Chemii : Zakład Chemii Organicznej | pl |
dc.contributor.author | Paradowska, Joanna | pl |
dc.contributor.author | Pasternak-Suder, Monika - 126154 | pl |
dc.contributor.author | Gut, Bartosz - 106417 | pl |
dc.contributor.author | Gryzło, Beata | pl |
dc.contributor.author | Młynarski, Jacek - 173385 | pl |
dc.date.accessioned | 2015-09-10T12:06:17Z | |
dc.date.available | 2015-09-10T12:06:17Z | |
dc.date.issued | 2012 | pl |
dc.description.number | 1 | pl |
dc.description.physical | 173-187 | pl |
dc.description.points | 35 | pl |
dc.description.volume | 77 | pl |
dc.identifier.doi | 10.1021/jo201584w | pl |
dc.identifier.eissn | 1520-6904 | pl |
dc.identifier.issn | 0022-3263 | pl |
dc.identifier.uri | http://ruj.uj.edu.pl/xmlui/handle/item/15530 | |
dc.language | eng | pl |
dc.language.container | eng | pl |
dc.rights | Dodaję tylko opis bibliograficzny | * |
dc.rights.licence | bez licencji | |
dc.rights.uri | * | |
dc.subtype | Article | pl |
dc.title | Direct asymmetric aldol reactions inspired by two types of natural aldolases : water-compatible organocatalysts and $Zn^{II}$ complexes | pl |
dc.title.journal | The Journal of Organic Chemistry | pl |
dc.type | JournalArticle | pl |
dspace.entity.type | Publication |