title: Organocatalytic enantioselective Michael addition of cyclic hemiacetals to nitroolefins: a facile access to chiral substituted 5- and 6-membered cyclic ethers.
abstract: An efficient aminocatalytic enantioselective Michael addition of readily available cyclic hemiacetals to nitroolefins has been developed. The strategy serves as a powerful approach to synthetically valuable chiral 3-substituted tetrahydrofurans (THFs) and tetrahydropyrans (THPs). The synthetic utilities of the versatile Michael adducts also have been demonstrated in the synthesis of 2,3-disubstituted cyclic ethers, α-substituted lactones and venlafaxine analogues.
authors: Jiangsu Key Laboratory of Translational Research and Therapy for Neuro-Psycho-Diseases & Department of Medicinal Chemistry, College of Pharmaceutical Sciences, Soochow University, 199 Ren'ai Road, Suzhou 215123, China. huyanwei@suda.edu.cn zhangshilei@suda.edu.cn.
authors: Yadong
authors: Y
authors: Zhu
authors: Pengfei
authors: P
authors: Qian
authors: Jiyang
authors: J
authors: Yang
authors: Shaohua
authors: S
authors: Chen
authors: Yanwei
authors: Y
authors: Hu
authors: Ping
authors: P
authors: Wu
authors: Wei
authors: W
authors: Wang
authors: Wei
authors: W
authors: Zhang
authors: Shilei
authors: S
authors: Zhang
mesh_terms: D000080:Acetals / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D000928:Antidepressive Agents / Q000138:chemical synthesis*; D002384:Catalysis; D003511:Cyclohexanols / Q000737:chemistry*; D015195:Drug Design; D004987:Ethers / Q000737:chemistry*; D004988:Ethers, Cyclic / Q000737:chemistry; D005663:Furans / Q000737:chemistry*; D007700:Kinetics; D007783:Lactones / Q000737:chemistry; D008956:Models, Chemical; D011714:Pyrans / Q000737:chemistry*; D013237:Stereoisomerism; D000069470:Venlafaxine Hydrochloride
chemical_list: D000080:Acetals; D000475:Alkenes; D000928:Antidepressive Agents; D003511:Cyclohexanols; D004987:Ethers; D004988:Ethers, Cyclic; D005663:Furans; D007783:Lactones; D011714:Pyrans; C018674:tetrahydrofuran; D000069470:Venlafaxine Hydrochloride