Jump to main content
Jump to site search
PLANNED MAINTENANCE Close the message box

Scheduled maintenance work on Wednesday 21st October 2020 from 07:00 AM to 07:00 PM (BST).

During this time our website performance may be temporarily affected. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 10, 2014
Previous Article Next Article

Asymmetric construction of quaternary stereocenters by magnesium catalysed direct amination of β-ketoesters using in situ generated nitrosocarbonyl compounds as nitrogen sources

Author affiliations

Abstract

The first example of a Lewis acid catalysed asymmetric hydroxyamination of β-ketoesters with nitrosocarbonyl compounds generated in situ was accomplished. The combination of a catalytic amount of Mg(OTf)2 with a chiral N,N′-dioxide ligand provides highly substituted quaternary β-keto amino acid derivatives in high yields (up to 97%) and enantioselectivities (up to 96%). Regioselectivities (N- vs. O-attack) are uniformly high for all substrates (>20 : 1).

Graphical abstract: Asymmetric construction of quaternary stereocenters by magnesium catalysed direct amination of β-ketoesters using in situ generated nitrosocarbonyl compounds as nitrogen sources

Back to tab navigation

Supplementary files

Article information


Submitted
02 May 2014
Accepted
13 Jun 2014
First published
16 Jun 2014

Chem. Sci., 2014,5, 3941-3945
Article type
Edge Article
Author version available

Asymmetric construction of quaternary stereocenters by magnesium catalysed direct amination of β-ketoesters using in situ generated nitrosocarbonyl compounds as nitrogen sources

B. Maji, M. Baidya and H. Yamamoto, Chem. Sci., 2014, 5, 3941
DOI: 10.1039/C4SC01272K

Social activity

Search articles by author

Spotlight

Advertisements