Catalytic Asymmetric Intramolecular Homologation of Ketones with α‐Diazoesters: Synthesis of Cyclic α‐Aryl/Alkyl β‐Ketoesters1. Issue 5 (8th December 2014)

• Record Type: Journal Article
• Authors: Li, Wei; Tan, Fei; Hao, Xiaoyu; Wang, Gang; Tang, Yu; Liu, Xiaohua; Lin, Lili; Feng, Xiaoming
• Is Part Of: Angewandte Chemie international edition. Volume 54:Issue 5(2015)
• Page Start: 1608
• Page End: 1611
• Publication Date: 2014-12-08
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201409572
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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.</p> </abstract>