Jump to main content
Jump to site search

Issue 73, 2015

The Mukaiyama aldol reaction of in situ generated nitrosocarbonyl compounds: selective C–N bond formation and N–O bond cleavage in one-pot for α-amination of ketones

Author affiliations

Abstract

A practical protocol for the α-amination of ketones (up to 99% yield) has been developed via the Mukaiyama aldol reaction of in situ generated nitrosocarbonyl compounds. The reaction with silyl enol ethers having a disilane (−SiMe2TMS) backbone proceeded not only with perfect N-selectivity but concomitant N–O bond cleavage was also accomplished. Such a cascade of C–N bond formation and N–O bond cleavage in a single step was heretofore unknown in the field of nitrosocarbonyl chemistry. A very high diastereoselectivity (dr = 19 : 1) was accomplished using (−)-menthol derived chiral nitrosocarbonyl compounds.

Graphical abstract: The Mukaiyama aldol reaction of in situ generated nitrosocarbonyl compounds: selective C–N bond formation and N–O bond cleavage in one-pot for α-amination of ketones

Supplementary files

Article information


Submitted
02 Jul 2015
Accepted
28 Jul 2015
First published
28 Jul 2015

Chem. Commun., 2015,51, 13976-13979
Article type
Communication
Author version available

The Mukaiyama aldol reaction of in situ generated nitrosocarbonyl compounds: selective C–N bond formation and N–O bond cleavage in one-pot for α-amination of ketones

I. Ramakrishna, G. S. Grandhi, H. Sahoo and M. Baidya, Chem. Commun., 2015, 51, 13976 DOI: 10.1039/C5CC05459A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.


Social activity

Search articles by author

Spotlight

Advertisements