新型吡咯烷基金属有机催化剂的合成及其在醛与硝基烯烃不对称迈克尔加成反应中的应用研究。
Synthesis of new pyrrolidine-based organocatalysts and study of their use in the asymmetric Michael addition of aldehydes to nitroolefins.
作者信息
Castán Alejandro, Badorrey Ramón, Gálvez José A, Díaz-de-Villegas María D
机构信息
Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), CSIC - Universidad de Zaragoza, Departamento de Química Orgánica, Pedro Cerbuna 12, E-50009 Zaragoza, Spain.
出版信息
Beilstein J Org Chem. 2017 Mar 27;13:612-619. doi: 10.3762/bjoc.13.59. eCollection 2017.
New pyrrolidine-based organocatalysts with a bulky substituent at C2 were synthesized from chiral imines derived from ()-glyceraldehyde acetonide by diastereoselective allylation followed by a sequential hydrozirconation/iodination reaction. The new compounds were found to be effective organocatalysts for the Michael addition of aldehydes to nitroolefins and enantioselectivities up to 85% ee were achieved.
通过非对映选择性烯丙基化反应，然后依次进行氢化锆化/碘化反应，从（）-甘油醛缩丙酮衍生的手性亚胺合成了在C2处带有庞大取代基的新型吡咯烷类有机催化剂。发现这些新化合物是醛与硝基烯烃迈克尔加成反应的有效有机催化剂，对映选择性高达85%ee。
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