Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 10691, Stockholm, Sweden.
Chemistry. 2023 Jan 12;29(3):e202203130. doi: 10.1002/chem.202203130. Epub 2022 Nov 22.
A novel iron-catalyzed borylation of propargylic acetates leading to allenylboronates has been developed. The method allows the preparation of a variety of di-, tri- and tetrasubstituted allenylboronates at room temperature with good functional group compatibility. Stereochemical studies show that an anti-S 2' displacement of acetate by boron occurs; this also allows transfer of chirality to yield enantiomerically enriched allenylboronates. The synthetic utility of this protocol was further substantiated by transformations of the obtained allenylboronates including oxidation and propargylation.
一种新型的铁催化炔丙基醋酸盐的硼化反应已经被开发出来，生成了烯丙基硼酸酯。该方法允许在室温下制备各种二取代、三取代和四取代的烯丙基硼酸酯，具有良好的官能团兼容性。立体化学研究表明，醋酸盐通过硼原子发生反式 S2'取代；这也允许手性转移，得到对映体富集的烯丙基硼酸酯。该协议的合成实用性还通过包括氧化和炔丙基化在内的获得的烯丙基硼酸酯的转化得到了进一步证实。
