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Carbohydrates as chiral controllers: synthesis of dihydrothieno [2,3-c] furanones

Carbohydrates as chiral controllers: synthesis of dihydrothieno [2,3-c] furanones
Carbohydrates as chiral controllers: synthesis of dihydrothieno [2,3-c] furanones
Chiral dihydrothiophenes derived from carbohydrates can be transformed into a novel class of bicyclic and highly functionalized chirons by treatment with NaH. A mechanistic rationale is proposed which is consistent with experimental observations and demonstrates the stereodiscriminating properties exerted by carbohydrate chains with different configurations.
diastereoselective cycloadditions, nitroalkenes
0957-4166
2261-2264
Avalos, Martín
55d2a59e-8c35-4028-b6c5-bfdd7ecda5a4
Babiano, Reyes
b7ffd91c-bacd-4372-ab99-fc30ac2450ae
Cintas, Pedro
29979233-8382-47a8-bde7-1faf4869308c
Clemente, Fernando R.
91b8c77e-79df-4a90-846a-fe0ffec1b090
Gordillo, Ruth
9d99d140-b76f-492b-bb9d-911aed5690fb
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Jiménez, José L.
074cc8fd-9ea1-41fc-b8b6-551d26e5fcd3
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Palacios, Juan C.
2c06e379-89b3-46b1-95c8-7f5057732f9f
Avalos, Martín
55d2a59e-8c35-4028-b6c5-bfdd7ecda5a4
Babiano, Reyes
b7ffd91c-bacd-4372-ab99-fc30ac2450ae
Cintas, Pedro
29979233-8382-47a8-bde7-1faf4869308c
Clemente, Fernando R.
91b8c77e-79df-4a90-846a-fe0ffec1b090
Gordillo, Ruth
9d99d140-b76f-492b-bb9d-911aed5690fb
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Jiménez, José L.
074cc8fd-9ea1-41fc-b8b6-551d26e5fcd3
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Palacios, Juan C.
2c06e379-89b3-46b1-95c8-7f5057732f9f

Avalos, Martín, Babiano, Reyes, Cintas, Pedro, Clemente, Fernando R., Gordillo, Ruth, Hursthouse, Michael B., Jiménez, José L., Light, Mark E. and Palacios, Juan C. (2001) Carbohydrates as chiral controllers: synthesis of dihydrothieno [2,3-c] furanones. Tetrahedron: Asymmetry, 12 (16), 2261-2264. (doi:10.1016/S0957-4166(01)00408-6).

Record type: Article

Abstract

Chiral dihydrothiophenes derived from carbohydrates can be transformed into a novel class of bicyclic and highly functionalized chirons by treatment with NaH. A mechanistic rationale is proposed which is consistent with experimental observations and demonstrates the stereodiscriminating properties exerted by carbohydrate chains with different configurations.

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More information

Published date: 2001
Keywords: diastereoselective cycloadditions, nitroalkenes

Identifiers

Local EPrints ID: 19384
URI: https://eprints.soton.ac.uk/id/eprint/19384
ISSN: 0957-4166
PURE UUID: 4d2f8d4e-6e17-454b-84a8-52b26e47784f
ORCID for Mark E. Light: ORCID iD orcid.org/0000-0002-0585-0843

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Date deposited: 13 Feb 2006
Last modified: 15 Jul 2019 19:27

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Contributors

Author: Martín Avalos
Author: Reyes Babiano
Author: Pedro Cintas
Author: Fernando R. Clemente
Author: Ruth Gordillo
Author: José L. Jiménez
Author: Mark E. Light ORCID iD
Author: Juan C. Palacios

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