The University of Southampton
University of Southampton Institutional Repository

Silver acetate catalysed asymmetric 1,3-dipolar cycloadditions of imines and chiral acrylamides

Silver acetate catalysed asymmetric 1,3-dipolar cycloadditions of imines and chiral acrylamides
Silver acetate catalysed asymmetric 1,3-dipolar cycloadditions of imines and chiral acrylamides
N-Metallated azomethine ylides 5 were generated by the reaction of arylidene glycine imines 1 with AgOAc and triethylamine. These azomethine ylides undergo cycloaddition to chiral acrylamides 2 with excellent diastereoselectivity. The configuration of two of the cycloadducts (3a(1) and 3c(1)) has been confirmed by Xray crystallography.
cycloaddition, azomethine ylides, pyrrolidine, asymmetric azomethine ylides, acid-esters, alkaloids, auxiliary
0936-5214
947-950
Nyerges, Miklós
346c6b55-e2a6-48fe-8f02-4d5c1f4c1d7a
Bendell, David
f7f9a24a-bc02-4a61-9841-5e6ec0d63db5
Arany, Andrea
217fb728-b3c1-4011-90c8-bfc0a6ea533c
Hibbs, David E.
92245583-6eb5-4afc-9093-57377cd6abf4
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Groundwater, Paul W.
b173ff4f-9897-4375-bbef-5d00779fc3a0
Meth-Cohn, Otto
d89b6869-cc40-461e-a085-a976ede4a33a
Nyerges, Miklós
346c6b55-e2a6-48fe-8f02-4d5c1f4c1d7a
Bendell, David
f7f9a24a-bc02-4a61-9841-5e6ec0d63db5
Arany, Andrea
217fb728-b3c1-4011-90c8-bfc0a6ea533c
Hibbs, David E.
92245583-6eb5-4afc-9093-57377cd6abf4
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Groundwater, Paul W.
b173ff4f-9897-4375-bbef-5d00779fc3a0
Meth-Cohn, Otto
d89b6869-cc40-461e-a085-a976ede4a33a

Nyerges, Miklós, Bendell, David, Arany, Andrea, Hibbs, David E., Coles, Simon J., Hursthouse, Michael B., Groundwater, Paul W. and Meth-Cohn, Otto (2003) Silver acetate catalysed asymmetric 1,3-dipolar cycloadditions of imines and chiral acrylamides. Synlett, (7), 947-950. (doi:10.1055/s-2003-39325).

Record type: Article

Abstract

N-Metallated azomethine ylides 5 were generated by the reaction of arylidene glycine imines 1 with AgOAc and triethylamine. These azomethine ylides undergo cycloaddition to chiral acrylamides 2 with excellent diastereoselectivity. The configuration of two of the cycloadducts (3a(1) and 3c(1)) has been confirmed by Xray crystallography.

This record has no associated files available for download.

More information

Published date: 1 June 2003
Keywords: cycloaddition, azomethine ylides, pyrrolidine, asymmetric azomethine ylides, acid-esters, alkaloids, auxiliary

Identifiers

Local EPrints ID: 20055
URI: http://eprints.soton.ac.uk/id/eprint/20055
ISSN: 0936-5214
PURE UUID: 5cfb817d-42c2-4a84-aaf7-5c7b5f65a5ee
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

Catalogue record

Date deposited: 24 Feb 2006
Last modified: 16 Mar 2024 03:05

Export record

Altmetrics

Contributors

Author: Miklós Nyerges
Author: David Bendell
Author: Andrea Arany
Author: David E. Hibbs
Author: Simon J. Coles ORCID iD
Author: Paul W. Groundwater
Author: Otto Meth-Cohn

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of http://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×