Access to Enantioenriched Allylic Alcohols via Peptide-Mimic Phosphonium Salt-Catalyzed Asymmetric Aerobic Hydroxylation  

作　　者：Jixing Che Siqiang Fang Zanjiao Liu Jiaja He Jia-Yan Zheng Fan Wang Tianli Wang 

机构地区：[1]Key Laboratory of Green Chemistry&Technology of Ministry of Education,College of Chemistry,Sichuan University,29 Wangjiang Road,Chengdu,Sichuan610064,China [2]Department of Chemistry,National University of Singapore,Science Drive 3,Singapore 117543,Singapore

出　　处：《Chinese Journal of Chemistry》2024年第17期2017-2022,共6页中国化学（英文版）

基　　金：Financial support was provided by the National Natural Science Foundation of China(22222109,21921002,22101189 and 22371190);the National Key R&DProgramof China(2018YFA0903500);Beijing National Laboratory for Molecular Sciences(BNLMs202101);Sichuan Science Foundation for Distinguished Young Scholars(2023NSFSC1921);Sichuan Provincial Natural Science Foundation(2022NSFSC1181,24NSFSC6590);Fundamental Research Funds from Sichuan University(2020SCUNL108)and Fundamental Research Funds for the Central Universities.

摘　　要：The development of catalytic asymmetric methods that enable access to value-added functionalities or structures,exemplified by allylic alcohols,is a highly interesting yet challenging topic from both academic and industrial perspectives.However,before recent advances in chemical catalysis,there were scarce protocols toward constructing enantioenriched tertiary allylic alcohol scaffolds.In this context,peptide-mimic phosphonium salts were found to be highly efficient in catalytic asymmetricα-hydroxylation ofα,β-unsaturated and/orβ,Y-unsaturated compounds with satisfactory regio-and stereochemical outcomes(up to 97%yield and 95%ee).This methodology tolerates a broad array of substrates and thus provides an expeditious and unified platform for the assembly of enantioenriched tertiary allylic alcohols by avoiding the use of additional reductants and expensive metal catalysts.Furthermore,the power of this protocol is enlarged by simple conditions and the use of air as a source of hydroxyl functionality.

关 键 词：Asymmetric catalysis Peptide-mimic phosphonium salts Aerobic hydroxylation Enantioenrichedα-allylic alcohols lon pairs Oxygen Ketones 

分 类 号：O62[理学—有机化学]