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
947-950
Nyerges, Miklós
346c6b55-e2a6-48fe-8f02-4d5c1f4c1d7a
Bendell, David
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Arany, Andrea
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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
1 June 2003
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), .
(doi:10.1055/s-2003-39325).
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.
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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
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Date deposited: 24 Feb 2006
Last modified: 16 Mar 2024 03:05
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Contributors
Author:
Miklós Nyerges
Author:
David Bendell
Author:
Andrea Arany
Author:
David E. Hibbs
Author:
Paul W. Groundwater
Author:
Otto Meth-Cohn
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