通过分子内Heck-Matsuda/羰基化/Stille偶联对3,3-二取代-2,3-二氢苯并呋喃进行对映选择性合成。

Leão Luiz Paulo Melchior de Oliveira, Köster Otto Daolio, Duarte Leonardo José, Braga Ataualpa Albert Carmo, Correia Carlos Roque Duarte

Chemistry Institute, State University of Campinas, Unicamp, 13083-970 Campinas, São Paulo, Brazil.

Department of Fundamental Chemistry, Institute of Chemistry, University of São Paulo, USP, 05508-900 São Paulo, São Paulo, Brazil.

J Org Chem. 2025 Jul 4;90(26):8835-8845. doi: 10.1021/acs.joc.4c02503. Epub 2025 Jun 25.

The enantioselective one-pot synthesis of 3,3-disubstituted-2,3-dihydrobenzofuran was developed via a strategy involving a palladium-catalyzed Heck-Matsuda reaction, followed by subsequent carbonylation and/or an organotin transmetalation step employing chiral , ligands. The one-pot reaction requires mild conditions and tolerates a wide range of functional groups. This method provides straightforward access to a diverse array of enantioenriched dihydrobenzofurans bearing a ketone or an alkyl side chain adjacent to the generated quaternary stereogenic center in yields up to 91% and er up to 99:1.

通过一种策略开发了3,3-二取代-2,3-二氢苯并呋喃的对映选择性一锅法合成，该策略包括钯催化的Heck-Matsuda反应，随后是羰基化和/或使用手性配体的有机锡转金属化步骤。该一锅法反应需要温和的条件，并且能耐受多种官能团。该方法提供了直接获得各种对映体富集的二氢苯并呋喃的途径，这些二氢苯并呋喃在生成的季碳立体中心附近带有酮或烷基侧链，产率高达91%，对映体过量比高达99:1。