与侧链硝基烯烃的分子内硅烷氧基-迈克尔反应：外消旋和对映选择性反应
Intramolecular Silanoxy-Michael Reactions with Pendant Nitroalkenes: Racemic and Enantioselective.
作者信息
Joshi Harshit, Sathyamoorthi Shyam
机构信息
Department of Medicinal Chemistry, University of Kansas, Lawrence, Kansas 66047, United States.
出版信息
J Org Chem. 2024 Oct 4;89(19):14197-14203. doi: 10.1021/acs.joc.4c01625. Epub 2024 Sep 21.
Abstract
We present the first racemic and scalemic examples of di--butyl silanoxy-Michael additions. Our operationally simple protocol is selective for nitro-olefins and simply involves stirring the substrate with an appropriate hydrogen-bond donor catalyst without any special precautions to exclude air or moisture. For each substrate examined, we have developed complementary protocols that optimize yield and enantioselectivity. Our reactions scale well, and the products are valuable intermediates for further transformations, including for the preparation of enantioenriched vicinal amino alcohols.
摘要
我们展示了二丁基硅烷氧基-迈克尔加成反应的首个外消旋和非外消旋实例。我们操作简单的方案对硝基烯烃具有选择性，只需将底物与合适的氢键供体催化剂搅拌即可，无需采取任何特殊措施来排除空气或水分。对于所研究的每种底物，我们都开发了互补的方案以优化产率和对映选择性。我们的反应具有良好的扩展性，产物是进一步转化的有价值中间体，包括用于制备对映体富集的邻位氨基醇。
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