Department of Chemistry, Pohang University of Science and Technology , 77 Cheongam-Ro, Nam-Gu, Pohang, Gyeongbuk 37673, Republic of Korea.
Center for Molecular Modeling and Simulation, Korea Research Institute of Chemical Technology , 141 Gajeongro, Yuseong-Gu, Daejeon 34114, Republic of Korea.
Org Lett. 2018 Feb 16;20(4):1248-1251. doi: 10.1021/acs.orglett.8b00191. Epub 2018 Feb 5.
A new palladium-catalyzed asymmetric addition reaction of indoles to alkoxyallenes is reported. Remarkably, the reaction showed complete regioselectivity toward the nitrogen. A new mechanism distinct from that of conventional π-allyl chemistry is proposed to explain this unique selectivity. The utility of the reaction is demonstrated by highly efficient and flexible synthesis of N-glycosylindoles.
报道了一种钯催化的吲哚与烷氧基丙二烯的新型不对称加成反应。值得注意的是，该反应对氮原子具有完全的区域选择性。提出了一种与传统π-烯丙基化学不同的新机制来解释这种独特的选择性。该反应的实用性通过高效、灵活的 N-糖基吲哚的合成得到了证明。
