文献类型：期刊文献

英文题名：Organocatalytic Asymmetric Formal [4+2] Cycloaddition of in Situ Oxidation-Generated ortho-Quinone Methides and Aldehydes

作者：Zhou, Ding[1];Yu, Xueting[1];Zhang, Jian[1];Wang, Wei[1,2];Xie, Hexin[1]

机构：[1]East China Univ Sci & Technol, Shanghai Key Lab New Drug Design, Sch Pharm, State Key Lab Bioreactor Engn, Shanghai 200237, Peoples R China;[2]Univ New Mexico, Dept Chem & Chem Biol, Albuquerque, NM 87131 USA

年份：2018

卷号：20

期号：1

起止页码：174

外文期刊名：ORGANIC LETTERS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000419749700045)，CCR-EXPANDED(收录号:WOS:000419749700045)】；

基金：We are thankful to the "Thousand Plan" Youth Program, the Fundamental Research Funds for the Central Universities, and the East China University of Science and Technology for financial support.

语种：英文

摘要：An unprecedented chiral secondary amine-catalyzed formal [4 + 2] annulation of aldehydes and oxidation generated beta-unsubstituted o-QMs is reported. This asymmetric protocol allows direct functionalization of the benzylic C-H bonds and furnishes [4 + 2] cycloadducts, chromanols, with excellent enantioselectivity and in up to 92% yield. The usability of this approach was further demonstrated by the enantioselective synthesis of anticancer Rhinacanthins derivative NKPLS8.