Wani Imtiyaz Ahmad, Sk Sahid, Mal Abhijit, Sengupta Arunava, Ghorai Manas K
Indian Institution of Technology Kanpur, Kanpur, Uttar Pradesh 208016, India.
Org Lett. 2022 Nov 4;24(43):7867-7872. doi: 10.1021/acs.orglett.2c02354. Epub 2022 Sep 12.
An unprecedented and novel synthetic route to hexahydropyrrolo[2,3-]indoles bearing -contiguous stereocenters with excellent stereoselectivities (ee of >99%, dr of ≤99:1) has been disclosed that proceeds through the ring opening of activated aziridines with electron deficient 4-substituted indoles followed by a novel cyclization in a domino fashion, thereby obviating the use of 3-substituted indoles as the prerequisite nucleophile. Another efficient synthetic route to tetrahydropyrrolo[4,3,2-]quinolines in excellent yields (≤93%) and excellent enantioselectivity (ee of >99%) has been established via ring opening of activated aziridines with 4-bromo-1-methyl-1-indole at relatively higher temperatures followed by Cu(I)-catalyzed intramolecular C-N cyclization in the same pot. The stability and the formation of products at different temperatures are explained by computational studies.
已公开了一种前所未有的新颖合成路线，用于制备具有连续立体中心且立体选择性优异（对映体过量率>99%，非对映体比例≤99:1）的六氢吡咯并[2,3 - ]吲哚，该路线通过活化氮丙啶与缺电子的4 - 取代吲哚开环，然后以多米诺方式进行新型环化反应，从而避免了使用3 - 取代吲哚作为必备亲核试剂。另一种高效合成路线用于制备产率优异（≤93%）且对映选择性优异（对映体过量率>99%）的四氢吡咯并[4,3,2 - ]喹啉，该路线是在相对较高温度下通过活化氮丙啶与4 - 溴 - 1 - 甲基 - 1 - 吲哚开环，然后在同一反应釜中进行铜（I）催化的分子内C - N环化反应。通过计算研究解释了不同温度下产物的稳定性和形成情况。
