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Highly efficient chiral polydentate sulfinyl ligands/catalysts containing prolinol moiety
Tetrahedron ( IF 2.1 ) Pub Date : 2016-04-29 08:46:01
Jacek Chrzanowski, Michał Rachwalski, Adam M. Pieczonka, Stanisław Leśniak, Józef Drabowicz, Piotr Kiełbasiński

New polydentate chiral ligands, containing the hydroxyl group, stereogenic sulfinyl group and enantiomeric prolinol moieties were synthesized and proved very efficient catalysts in the asymmetric diethylzinc addition to benzaldehyde, the asymmetric aldol condensation and the asymmetric Mannich reaction. Replacement of the central hydroxyl group with the second prolinol moiety of the same absolute configuration gave new ligands in which the sulfinyl group was not a stereogenic centre anymore, but which proved almost equally efficient as catalysts for the reactions investigated. The absolute configuration of the proline moiety exerted a decisive impact on the stereochemical outcome of these reactions, deciding about the absolute configuration of the products formed.

中文翻译:

含有脯氨醇部分的高效手性多齿亚磺酰基配体/催化剂

合成了含有羟基,立体亚砜基和对映脯氨醇部分的新的多齿手性配体,并证明了其在苯甲醛,不对称醛醇缩合和不对称曼尼希反应等不对称二乙基锌中的催化效果非常好。用相同绝对构型的第二脯氨醇部分取代中心羟基,得到新的配体,其中亚磺酰基不再是立体异构中心,但事实证明与研究的催化剂几乎一样有效。脯氨酸部分的绝对构型对这些反应的立体化学结果具有决定性的影响,决定了所形成产物的绝对构型。
更新日期:2016-04-30
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