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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 were generated by the reaction of arylidene glycine imines with AgOAc and triethylamine. These azomethine ylides undergo cycloaddition to chiral acrylamides with excellent diastereoselectivity. The configuration of two of the cycloadducts was confirmed by X-ray crystallography.
amines, asymmetric, azomethine ylide, cycloaddition, pyrrolidine didehydroamino acid-esters, formal total synthesis, azomethine ylides, amino-acids, derivatives, amides, auxiliary, acrylate, ring
0040-4020
3745-3753
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.
65bb28e4-4917-43f5-a770-a00017d6783f
Hursthouse, Michael B.
a65b4d35-2ea0-47e7-938a-d744f4d9ba28
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.
65bb28e4-4917-43f5-a770-a00017d6783f
Hursthouse, Michael B.
a65b4d35-2ea0-47e7-938a-d744f4d9ba28
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 (2005) Silver acetate-catalysed asymmetric 1,3-dipolar cycloadditions of imines and chiral acrylamides. Tetrahedron, 61 (15), 3745-3753. (doi:10.1016/j.tet.2005.02.009).

Record type: Article

Abstract

N-Metallated azomethine ylides were generated by the reaction of arylidene glycine imines with AgOAc and triethylamine. These azomethine ylides undergo cycloaddition to chiral acrylamides with excellent diastereoselectivity. The configuration of two of the cycloadducts was confirmed by X-ray crystallography.

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More information

Published date: 11 April 2005
Keywords: amines, asymmetric, azomethine ylide, cycloaddition, pyrrolidine didehydroamino acid-esters, formal total synthesis, azomethine ylides, amino-acids, derivatives, amides, auxiliary, acrylate, ring

Identifiers

Local EPrints ID: 20877
URI: http://eprints.soton.ac.uk/id/eprint/20877
ISSN: 0040-4020
PURE UUID: 50ad258f-8e46-443e-bc50-f0fdf695a050

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Date deposited: 02 Mar 2006
Last modified: 15 Jul 2019 19:25

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Contributors

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

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