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Direct enantioselective synthesis of bicyclic Diels–Alder products

Direct enantioselective synthesis of bicyclic Diels–Alder products
Direct enantioselective synthesis of bicyclic Diels–Alder products
The direct amine-catalyzed enantioselective Diels–Alder reaction between ?,?-unsaturated cyclic ketones and nitroolefins is presented. A simple diamine catalyzes the asymmetric Diels–Alder reaction with high stereoselectivity and furnishes the corresponding Diels–Alder adducts in good to high yields with >25:1 dr and up to 86?% ee. The study demonstrates a convenient entry to functionalized bicyclic molecules contaning four stereocenters that are formed with excellent diastreoselectivity and good to high enantioselectivity.
asymmetric catalysis, diels–alder reaction, nitroolefins, organocatalysis, ?, ?-unsaturated cyclic ketones
1615-4150
2549-2555
Sundén, Henrik
fe114b08-1de1-4e88-9778-a9cddf3aa76d
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Xu, Yongmei
77a1cd82-b3af-4fab-bb76-23523d8224a0
Eriksson, Lars
340ffb17-9c8e-468f-acba-13219dc22c37
Córdova, Armando
d2a1239f-708d-4f9c-bf7c-c095e9a27cac
Sundén, Henrik
fe114b08-1de1-4e88-9778-a9cddf3aa76d
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Xu, Yongmei
77a1cd82-b3af-4fab-bb76-23523d8224a0
Eriksson, Lars
340ffb17-9c8e-468f-acba-13219dc22c37
Córdova, Armando
d2a1239f-708d-4f9c-bf7c-c095e9a27cac

Sundén, Henrik, Rios, Ramon, Xu, Yongmei, Eriksson, Lars and Córdova, Armando (2007) Direct enantioselective synthesis of bicyclic Diels–Alder products. Advanced Synthesis & Catalysis, 349 (17-18), 2549-2555. (doi:10.1002/adsc.200700175).

Record type: Article

Abstract

The direct amine-catalyzed enantioselective Diels–Alder reaction between ?,?-unsaturated cyclic ketones and nitroolefins is presented. A simple diamine catalyzes the asymmetric Diels–Alder reaction with high stereoselectivity and furnishes the corresponding Diels–Alder adducts in good to high yields with >25:1 dr and up to 86?% ee. The study demonstrates a convenient entry to functionalized bicyclic molecules contaning four stereocenters that are formed with excellent diastreoselectivity and good to high enantioselectivity.

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More information

e-pub ahead of print date: 27 November 2007
Published date: 10 December 2007
Keywords: asymmetric catalysis, diels–alder reaction, nitroolefins, organocatalysis, ?, ?-unsaturated cyclic ketones
Organisations: Chemistry

Identifiers

Local EPrints ID: 347979
URI: http://eprints.soton.ac.uk/id/eprint/347979
ISSN: 1615-4150
PURE UUID: 23e1c1d0-68f1-4d00-9694-4c50641973cf
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

Catalogue record

Date deposited: 05 Feb 2013 10:03
Last modified: 26 Nov 2019 01:37

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