5724-06-1Relevant articles and documents
Synthesis of Antitricyclic Morpholine Derivatives through Iodine(III)-Mediated Intramolecular Umpolung Cycloaddition of Olefins
Deng, Qingfu,Feng, Yangyang,Xiong, Ruimei,Xiong, Yan,Yang, Chenglin,Zhang, Xiaohui
, p. 4500 - 4506 (2020/04/09)
A (diacetoxyiodo)benzene-mediated intramolecular cycloaddition of olefins to construct tricyclic morpholines is presented. A series of substituted tricyclic morpholines were obtained in one-step simple operation under mild conditions, and the NMR studies
HFIP Solvent Enables Alcohols to Act as Alkylating Agents in Stereoselective Heterocyclization
Zhu, Yuxiang,Colomer, Ignacio,Thompson, Amber L.,Donohoe, Timothy J.
supporting information, p. 6489 - 6493 (2019/05/06)
A new method for the stereoselective synthesis of highly functionalized oxygen heterocycles using allyl or benzyl alcohols as alkylating agents is presented. The process is efficient and atom economic, generating water as the only stoichiometric byproduct. Substoichiometric amounts of Ti(OiPr)4 in HFIP solvent are key to this reactivity, and the method tolerates a broad substitution pattern on both the alcohol initiator and homoallylic alcohol substrate. Preliminary mechanistic studies reveal in situ formation of a titanium complex with HFIP which may initiate the cyclization reaction. Further stereoselective functionalization of the products allows access to a diverse range of interesting heterocyclic structures.
Reversing the Regioselectivity of Halofunctionalization Reactions through Cooperative Photoredox and Copper Catalysis
Griffin, Jeremy D.,Cavanaugh, Cortney L.,Nicewicz, David A.
supporting information, p. 2097 - 2100 (2017/02/15)
Halofunctionalization of alkenes is a classical method for olefin difunctionalization. It gives rise to adducts which are found in many natural products and biologically active molecules, and offers a synthetic handle for further manipulation. Classically, this reaction is performed with an electrophilic halogen source and leads to regioselective formation of the halofunctionalized adducts. Herein, we demonstrate a reversal of the native regioselectivity for alkene halofunctionalization through the use of an acridinium photooxidant in conjunction with a copper cocatalyst.