Allylic amines and 1,3-oxazinanes are valuable molecular skeletons in organic synthesis and pharmaceutical industry.A straightforward way to such two types of compounds by solvent-controlled rare-earth metal Lewis aci...Allylic amines and 1,3-oxazinanes are valuable molecular skeletons in organic synthesis and pharmaceutical industry.A straightforward way to such two types of compounds by solvent-controlled rare-earth metal Lewis acid-catalyzed transformations of 2-(hetero)aryl-N-sulfonylazetidines:the ring-opening isomerization of azetidines to allylic amines and the annulation of azetidines with aldehydes to 1,3-oxazinanes are reported.These two reactions feature scalability,low catalyst loading,mild reaction conditions,excellent yields and regioselectivity with demonstrated utility in three-step product transformations to naftifine,abamine and abamine SG.展开更多
Novel C-17-chloro-substituted derivative of vinorelbine or vinflunine has been regio-selectively synthesized via the chlorination reaction in the presence of Lewis acid.The catalyst Cp2TiCl2 plays a key role in the ch...Novel C-17-chloro-substituted derivative of vinorelbine or vinflunine has been regio-selectively synthesized via the chlorination reaction in the presence of Lewis acid.The catalyst Cp2TiCl2 plays a key role in the chlorination reaction.展开更多
Electrochemistry contributes a strong tool for the manufacture of molecules,addressing intractable challenges in synthetic chemistry by enabling innovative reaction pathways.Herein,a bifunctional reagent,aqueous hydro...Electrochemistry contributes a strong tool for the manufacture of molecules,addressing intractable challenges in synthetic chemistry by enabling innovative reaction pathways.Herein,a bifunctional reagent,aqueous hydrochloric acid,is used to establish an electrochemical selective dual-oxidation approach that gives access toα-chlorosulfoxides from sulfides.This strategy presents broad substrate scope,high diastereoselectivity,and regioselectivity.The late-stage modification of amino acids and pharmaceutical derivatives further highlights the utility.Furthermore,detailed mechanistic studies reveal that the key success for this selective chemical transformation is the dual-oxidation process at the anode.This electrochemical dual-oxidation strategy may have wide universality;we anticipate diverse applications of this protocol across the many fields of chemistry.展开更多
A visible light-mediated approach for the preparation of α-bromo-α,β-unsaturated ketones and aldehydes was developed. In comparison to traditional methods that generally take two steps to afford the above compounds...A visible light-mediated approach for the preparation of α-bromo-α,β-unsaturated ketones and aldehydes was developed. In comparison to traditional methods that generally take two steps to afford the above compounds, this protocol was highlighted by its operational simplicity, avoiding using hazardous bromine and mild reaction conditions.展开更多
文摘Allylic amines and 1,3-oxazinanes are valuable molecular skeletons in organic synthesis and pharmaceutical industry.A straightforward way to such two types of compounds by solvent-controlled rare-earth metal Lewis acid-catalyzed transformations of 2-(hetero)aryl-N-sulfonylazetidines:the ring-opening isomerization of azetidines to allylic amines and the annulation of azetidines with aldehydes to 1,3-oxazinanes are reported.These two reactions feature scalability,low catalyst loading,mild reaction conditions,excellent yields and regioselectivity with demonstrated utility in three-step product transformations to naftifine,abamine and abamine SG.
基金the National Natural Science Foundation of China (20872019)Fudan University for the research financial support
文摘Novel C-17-chloro-substituted derivative of vinorelbine or vinflunine has been regio-selectively synthesized via the chlorination reaction in the presence of Lewis acid.The catalyst Cp2TiCl2 plays a key role in the chlorination reaction.
基金supported by the National Natural Science Foundation of China(22031008)Science Foundation of Wuhan(2020010601012192)The Program of Introducing Talents of Discipline to Universities of China(111 Program)is also appreciated。
文摘Electrochemistry contributes a strong tool for the manufacture of molecules,addressing intractable challenges in synthetic chemistry by enabling innovative reaction pathways.Herein,a bifunctional reagent,aqueous hydrochloric acid,is used to establish an electrochemical selective dual-oxidation approach that gives access toα-chlorosulfoxides from sulfides.This strategy presents broad substrate scope,high diastereoselectivity,and regioselectivity.The late-stage modification of amino acids and pharmaceutical derivatives further highlights the utility.Furthermore,detailed mechanistic studies reveal that the key success for this selective chemical transformation is the dual-oxidation process at the anode.This electrochemical dual-oxidation strategy may have wide universality;we anticipate diverse applications of this protocol across the many fields of chemistry.
基金supported by the National Natural Science Foundation of China(2100201821072038+3 种基金2147203021302029)the State Key Laboratory of Urban Water Resource and Environment(2015DX01)the Fundamental Research Funds for the Central Universities(HIT.BRETIV.201310)
文摘A visible light-mediated approach for the preparation of α-bromo-α,β-unsaturated ketones and aldehydes was developed. In comparison to traditional methods that generally take two steps to afford the above compounds, this protocol was highlighted by its operational simplicity, avoiding using hazardous bromine and mild reaction conditions.
