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Organocatalytic enantioselective aminosulfenylation of alpha,beta-unsaturated aldehydes

Organocatalytic enantioselective aminosulfenylation of alpha,beta-unsaturated aldehydes
Organocatalytic enantioselective aminosulfenylation of alpha,beta-unsaturated aldehydes
A simple, highly enantioselective organocatalytic aminosulfenylation of ?,?-unsaturated aldehydes affords orthogonally protected ?-amino-?-mercaptoaldehydes in high yields and 93 to >99?%?ee (see scheme, Bn=benzyl). Notably, the catalytic transformation shows that it is possible to efficiently employ all components of an electrophile, which includes a nucleofuge, in organocatalytic domino reactions of enals.
aldehydes, asymmetric catalysis, domino reactions, nucleophilic substitution, organocatalysis
1433-7851
8468-8472
Zhao, Gui-Ling
106737c0-2aeb-4805-a8d7-496b1ce04322
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Vesely, Jan
1853ff19-a906-4321-bd69-f7e434176fc3
Eriksson, Lars
340ffb17-9c8e-468f-acba-13219dc22c37
Córdova, Armando
d2a1239f-708d-4f9c-bf7c-c095e9a27cac
Zhao, Gui-Ling
106737c0-2aeb-4805-a8d7-496b1ce04322
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Vesely, Jan
1853ff19-a906-4321-bd69-f7e434176fc3
Eriksson, Lars
340ffb17-9c8e-468f-acba-13219dc22c37
Córdova, Armando
d2a1239f-708d-4f9c-bf7c-c095e9a27cac

Zhao, Gui-Ling, Rios, Ramon, Vesely, Jan, Eriksson, Lars and Córdova, Armando (2008) Organocatalytic enantioselective aminosulfenylation of alpha,beta-unsaturated aldehydes. Angewandte Chemie International Edition, 47 (44), 8468-8472. (doi:10.1002/anie.200802335). (PMID:18821533)

Record type: Article

Abstract

A simple, highly enantioselective organocatalytic aminosulfenylation of ?,?-unsaturated aldehydes affords orthogonally protected ?-amino-?-mercaptoaldehydes in high yields and 93 to >99?%?ee (see scheme, Bn=benzyl). Notably, the catalytic transformation shows that it is possible to efficiently employ all components of an electrophile, which includes a nucleofuge, in organocatalytic domino reactions of enals.

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e-pub ahead of print date: 26 September 2008
Published date: 20 October 2008
Keywords: aldehydes, asymmetric catalysis, domino reactions, nucleophilic substitution, organocatalysis
Organisations: Chemistry
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Identifiers

Local EPrints ID: 347775
URI: http://eprints.soton.ac.uk/id/eprint/347775
DOI: doi:10.1002/anie.200802335
ISSN: 1433-7851
PURE UUID: 4a955368-baef-4eec-b1b4-907d9c344e10
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

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Date deposited: 30 Jan 2013 09:54
Last modified: 14 Mar 2024 12:51

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Contributors

Author: Gui-Ling Zhao
Author: Ramon Rios ORCID iD
Author: Jan Vesely
Author: Lars Eriksson
Author: Armando Córdova

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