Baby Stephin, Sakla Akash P, Sahu Bichismita
Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Ahmedabad, Gujarat 382355, India.
Org Lett. 2025 Sep 19;27(37):10377-10382. doi: 10.1021/acs.orglett.5c03184. Epub 2025 Sep 8.
Herein, we report an easily tunable and regioselective Pd-catalyzed allene-alkyne coupling protocol for the stereodivergent synthesis of - and -1,3-enynes using purine allenamine by a simple switch of ligands P(-tolyl)Ph and Boc-Phe-OH. For the first time, we have explored mono--protected amino acids (MPAAs) as ligands in allene-alkyne coupling to furnish -1,3-enynes selectively. This protocol streamlined the access to chiral 1,3-enynes and addressed the long-standing stereoselectivity challenges associated with 1,3-enynes from allene-alkyne coupling.
在此，我们报道了一种易于调节且具有区域选择性的钯催化丙二烯-炔烃偶联反应，该反应通过简单切换配体P(-tolyl)Ph和Boc-Phe-OH，利用嘌呤烯丙胺实现了立体发散合成 - 和 -1,3-烯炔。我们首次探索了单-保护氨基酸（MPAAs）作为丙二烯-炔烃偶联反应中的配体，以选择性地提供 -1,3-烯炔。该反应简化了手性1,3-烯炔的合成，并解决了丙二烯-炔烃偶联反应中与1,3-烯炔相关的长期存在的立体选择性挑战。
