Enantioselective methodologies using N-carbamoyl-imines

Nucleophilic addition to carbon-nitrogen double bonds (imines) represents one of the most common strategies for the synthesis of amine derivatives. In order to circumvent the problem associated with low reactivity of imines in nucleophilic addition, various imines with electron-withdrawing groups at...

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Bibliographic Details
Published in:Chemical Society reviews 2014-01, Vol.43 (2), p.611-63
Main Authors: Vesely, Jan, Rios, Ramon
Format: Article
Language:English
Subjects:
Amines
Asymmetry
Derivatives
Imines
Nucleophiles
Organic compounds
Strategy
Synthesis
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Summary:Nucleophilic addition to carbon-nitrogen double bonds (imines) represents one of the most common strategies for the synthesis of amine derivatives. In order to circumvent the problem associated with low reactivity of imines in nucleophilic addition, various imines with electron-withdrawing groups at nitrogen have been studied, and many of them were successfully applied in asymmetric methodologies. Especially N -carbamoyl imines were found to be useful in the enantioselective synthesis of various organic compounds, due to their increased reactivity toward nucleophiles as well as limited difficulties connected with the removal of the carbamoyl moiety in target molecules. The aim of this review is to cover enantioselective methods based on N -carbamoyl imines, focusing on synthetically useful protocols. N -Carbamoyl imines have been shown to be versatile and useful reagents for the synthesis of amino derivatives.
ISSN:0306-0012
1460-4744
DOI:10.1039/c3cs60321k