Department of Chemistry , University of Utah , 315 S 1400 E , Salt Lake City , Utah 84112 , United States.
J Am Chem Soc. 2019 Jun 5;141(22):8670-8674. doi: 10.1021/jacs.9b01476. Epub 2019 May 24.
The development of an intermolecular and enantioselective aza-Wacker reaction is described. Using indoles as the N-source and a selection of alkenols as the coupling partners selective β-hydride elimination toward the alcohol was achieved. This strategy preserves the newly formed stereocenter by preventing the formation of traditionally observed enamine products. Allylic and homoallylic alcohols with a variety of functional groups are compatible with the reaction in high enantioselectivity. Isotopic-labeling experiments support a syn amino-palladation mechanism for this new class of aza-Wacker reactions.
本文描述了一种分子间对映选择性的氮杂-Wacker 反应的发展。以吲哚作为氮源，选择一系列烯醇作为偶联试剂，通过β-氢消除实现了对醇的选择性。该策略通过防止传统观察到的烯胺产物的形成，保留了新形成的立体中心。具有各种官能团的烯丙基和同烯丙基醇在高对映选择性下与反应兼容。同位素标记实验支持了此类新型氮杂-Wacker 反应的顺氨钯化反应机制。
