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Organocatalytic Asymmetric Conjugate Addition of Aldehydes to Nitroolefins : Identification of Catalytic Intermediates and the Stereoselectivity-Determining Step by ESI-MS

Bächle, Florian and Duschmalé, Jörg and Ebner, Christian and Pfaltz, Andreas and Wennemers, Helma. (2013) Organocatalytic Asymmetric Conjugate Addition of Aldehydes to Nitroolefins : Identification of Catalytic Intermediates and the Stereoselectivity-Determining Step by ESI-MS. Angewandte Chemie International Edition, 52 (48). pp. 12619-12623.

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Official URL: http://edoc.unibas.ch/dok/A6212003

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Abstract

Looking back: The asymmetric organocatalytic 1,4-addition of aldehydes to nitroolefins was studied by ESI-MS. Analysis of the back reaction starting from quasienantiomeric mass-labeled 1,4-adducts provided conclusive evidence for an enamine rather than an enol mechanism, and allowed identification of the enantioselectivity-determining step.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Synthetische organische Chemie (Pfaltz)
UniBasel Contributors:Pfaltz, Andreas and Bächle, Florian
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Wiley
ISSN:1433-7851
e-ISSN:1521-3773
Note:Publication type according to Uni Basel Research Database: Journal article
Identification Number:
Last Modified:10 Apr 2017 08:49
Deposited On:31 Jan 2014 09:51

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