Department of Chemistry, University of Chicago, 5735 South Ellis Avenue, Chicago, IL, 60637, USA.
Angew Chem Int Ed Engl. 2017 Aug 7;56(33):9962-9966. doi: 10.1002/anie.201705322. Epub 2017 Jul 12.
The asymmetric synthesis of (-)-N-methylwelwitindolinone B isothiocyanate is reported. Critical challenges overcome through these studies include the stereoselective installation of the sterically congested C13 alkyl chloride and control of the wayward reactivity of the indole unit to standard oxidants. A Pt-catalyzed hydrosilylation helped stymie unwanted rearrangements facilitated by vinyl group participation during the chloride installation step, and a new Fe -catalyzed oxidation accomplished the problematic conversion of indole into 2-indolinone.
本文报道了（-）-N-甲基威尔witindolinone B 异硫氰酸酯的不对称合成。通过这些研究克服的关键挑战包括立体选择性地安装空间位阻较大的 C13 烷基氯，以及控制吲哚单元对标准氧化剂的异常反应性。Pt 催化的硅氢化反应有助于阻止在氯化物安装步骤中由于乙烯基参与而导致的不需要的重排，而新的 Fe 催化氧化则完成了将吲哚转化为 2-吲哚啉酮的难题转化。
