Jump to main content
Jump to site search


Asymmetric catalytic construction of fully substituted carbon stereocenters using acyclic α-branched β-ketocarbonyls: the “Methyl Rule” widely exists

Author affiliations

Abstract

The catalytic asymmetric construction of tetrasubstituted carbon stereocenters constitutes one of the most challenging research topics in organic synthesis, which further plays vital roles in diverse fields including medicinal and materials chemistry. In this context, the α-functionalization of β-ketocarbonyl compounds serves as one of the most frequently used strategies to address the issue. Compared to cyclic β-ketocarbonyls, the catalytic asymmetric α-functionalization of acyclic β-ketocarbonyls is more difficult but has gained enough progress over the last several decades. This review illustrates the recent advances in this field, including asymmetric fluorination with acyclic α-branched β-ketocarbonyl participation, Michael addition, amination, aldol reaction, α-alkylation, α-alkynylation, α-oxygenation, Mannich reaction, etc. Furthermore, a thorough survey of all these reactions indicates the existence of a general principle which is called the “Methyl Rule”. Alternative methods that can complement the deficiency of reports of the use of direct asymmetric catalysis are also presented.

Graphical abstract: Asymmetric catalytic construction of fully substituted carbon stereocenters using acyclic α-branched β-ketocarbonyls: the “Methyl Rule” widely exists

Back to tab navigation

Article information


Submitted
08 Jun 2020
Accepted
20 Aug 2020
First published
20 Aug 2020

Org. Chem. Front., 2020, Advance Article
Article type
Review Article

Asymmetric catalytic construction of fully substituted carbon stereocenters using acyclic α-branched β-ketocarbonyls: the “Methyl Rule” widely exists

D. Sun, S. Yang and X. Fang, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO00673D

Social activity

Search articles by author

Spotlight

Advertisements