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Unexpected formation of ?-lactams and penem isosteres from mesoionics: sequential ring-opening-rearrangement of [3+2] cycloadducts

Unexpected formation of ?-lactams and penem isosteres from mesoionics: sequential ring-opening-rearrangement of [3+2] cycloadducts
Unexpected formation of ?-lactams and penem isosteres from mesoionics: sequential ring-opening-rearrangement of [3+2] cycloadducts
A novel and simple method has been developed to obtain penem analogs with biologically interesting functionalities, which combines aromatic aldehydes with thioisomunchnones, a readily available class of mesoionic heterocycles.
diastereoselective synthesis, cycloaddition chemistry, systems
1359-7345
1589-1590
Avalos, Martin
75b746b8-64d3-4451-be7a-c7c536ed6602
Babiano, Reyes
b7ffd91c-bacd-4372-ab99-fc30ac2450ae
Cintas, Pedro
29979233-8382-47a8-bde7-1faf4869308c
Jiménez, José L.
074cc8fd-9ea1-41fc-b8b6-551d26e5fcd3
López, Ignacio
215a6254-7805-40e9-a90d-878a966e6dbb
Palacios, Juan C.
2c06e379-89b3-46b1-95c8-7f5057732f9f
Hursthouse, Michael B.
a65b4d35-2ea0-47e7-938a-d744f4d9ba28
Light, Mark E.
13b5eb33-3114-4fb7-8500-90ce69e9933c
Avalos, Martin
75b746b8-64d3-4451-be7a-c7c536ed6602
Babiano, Reyes
b7ffd91c-bacd-4372-ab99-fc30ac2450ae
Cintas, Pedro
29979233-8382-47a8-bde7-1faf4869308c
Jiménez, José L.
074cc8fd-9ea1-41fc-b8b6-551d26e5fcd3
López, Ignacio
215a6254-7805-40e9-a90d-878a966e6dbb
Palacios, Juan C.
2c06e379-89b3-46b1-95c8-7f5057732f9f
Hursthouse, Michael B.
a65b4d35-2ea0-47e7-938a-d744f4d9ba28
Light, Mark E.
13b5eb33-3114-4fb7-8500-90ce69e9933c

Avalos, Martin, Babiano, Reyes, Cintas, Pedro, Jiménez, José L., López, Ignacio, Palacios, Juan C., Hursthouse, Michael B. and Light, Mark E. (1999) Unexpected formation of ?-lactams and penem isosteres from mesoionics: sequential ring-opening-rearrangement of [3+2] cycloadducts. Chemical Communications, (16), 1589-1590. (doi:10.1039/a904333k).

Record type: Article

Abstract

A novel and simple method has been developed to obtain penem analogs with biologically interesting functionalities, which combines aromatic aldehydes with thioisomunchnones, a readily available class of mesoionic heterocycles.

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More information

Published date: 1999
Keywords: diastereoselective synthesis, cycloaddition chemistry, systems

Identifiers

Local EPrints ID: 39135
URI: http://eprints.soton.ac.uk/id/eprint/39135
ISSN: 1359-7345
PURE UUID: 4809896c-d454-48b0-9260-a38c90cafcc1

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Date deposited: 18 Jul 2006
Last modified: 15 Jul 2019 19:01

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Contributors

Author: Martin Avalos
Author: Reyes Babiano
Author: Pedro Cintas
Author: José L. Jiménez
Author: Ignacio López
Author: Juan C. Palacios
Author: Michael B. Hursthouse
Author: Mark E. Light

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