Proline-Catalyzed Asymmetric α-Amination of Aldehydes and Ketones-An Astonishingly Simple Access to Optically Active α-Hydrazino Carbonyl Compounds

Simple, direct, and highly enantioselective α‐amination of carbonyl compounds 1 with azodicarboxylates 2 no longer requires prior enolization of the substrate. The “magic” small‐organic‐molecule catalyst for this reaction in dichloromethane at room temperature is once again L‐proline (3)....

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 42; no. 9; pp. 975 - 978
Main Author Duthaler, Rudolf O.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 03.03.2003
WILEY‐VCH Verlag
Subjects
Aldehydes - chemistry
Amination
Amines - chemical synthesis
azodicarboxylates
Catalysis
enantioselectivity
Ketones - chemistry
Molecular Structure
proline
Proline - chemistry
Stereoisomerism
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Summary:Simple, direct, and highly enantioselective α‐amination of carbonyl compounds 1 with azodicarboxylates 2 no longer requires prior enolization of the substrate. The “magic” small‐organic‐molecule catalyst for this reaction in dichloromethane at room temperature is once again L‐proline (3).
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200390283