title: Open-close: an alternative strategy to α-functionalization of lactone via enamine catalysis in one pot under mild conditions.
abstract: An open-close strategy in asymmetric catalysis is newly developed. With this powerful strategy, lactols are directly applied as potential precursors of lactones in enamine-based asymmetric Michael reactions providing a facile access to α-functionalized lactones containing two adjacent stereogenic centers as a single diastereomer in good to excellent yields (up to 99%) and with excellent enantioselectivities (most cases >99%). Moreover, the reaction products are shown to give highly functionalized derivatives by stepwise systematic transformations.
authors: †Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. China.
authors: Yan-Kai
authors: YK
authors: Liu
authors: ‡School of Life Science and Engineering, Southwest Jiaotong University, Chengdu, Sichuan 610031, P. R. China.
authors: Zhi-Long
authors: ZL
authors: Li
authors: †Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. China.
authors: Ji-Yao
authors: JY
authors: Li
authors: †Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. China.
authors: Huan-Xi
authors: HX
authors: Feng
authors: ‡School of Life Science and Engineering, Southwest Jiaotong University, Chengdu, Sichuan 610031, P. R. China.
authors: Zhi-Ping
authors: ZP
authors: Tong
mesh_terms: D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000588:Amines; D007783:Lactones