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Catalytic Asymmetric Intramolecular Homologation of Ketones with α‐Diazoesters: Synthesis of Cyclic α‐Aryl/Alkyl β‐Ketoesters
Author(s) -
Li Wei,
Tan Fei,
Hao Xiaoyu,
Wang Gang,
Tang Yu,
Liu Xiaohua,
Lin Lili,
Feng Xiaoming
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201409572
Subject(s) - stereocenter , intramolecular force , chemistry , aryl , alkyl , ketone , catalysis , yield (engineering) , medicinal chemistry , enantiomer , stereochemistry , enantioselective synthesis , organic chemistry , materials science , metallurgy
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.