Catalytic Asymmetric Intramolecular Homologation of Ketones with α‐Diazoesters: Synthesis of Cyclic α‐Aryl/Alkyl β‐Ketoesters |
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| Authors: | Dr Wei Li Fei Tan Xiaoyu Hao Gang Wang Yu Tang Prof?Dr Xiaohua Liu Dr Lili Lin Prof?Dr Xiaoming Feng |
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| Affiliation: | Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China) |
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| Abstract: | A catalytic asymmetric intramolecular homologation of simple ketones with α‐diazoesters was firstly accomplished with a chiral N,N′‐dioxide–Sc(OTf)3 complex. This method provides an efficient access to chiral cyclic α‐aryl/alkyl β‐ketoesters containing an all‐carbon quaternary stereocenter. Under mild conditions, a variety of aryl‐ and alkyl‐substituted ketone groups reacted with α‐diazoester groups smoothly through an intramolecular addition/rearrangement process, producing the β‐ketoesters in high yield and enantiomeric excess. |
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| Keywords: | asymmetric catalysis homologation scandium α ‐diazoesters β ‐ketoesters |
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