Organocatalyzed Asymmetric α-Aminoxylation of Aldehydes and Ketones-An Efficient Access to Enantiomerically Pure α-Hydroxycarbonyl Compounds, Diols, and Even Amino Alcohols

The magic of no metal: Enantiomerically pure α‐hydroxy aldehydes and ketones as well as diols can be synthesized by a direct (S)‐proline‐catalyzed asymmetric nitroso‐aldol reaction between the parent carbonyl compound and nitrosobenzene. Further elaboration of the obtained adducts provides useful pr...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2004-06, Vol.43 (23), p.2995-2997
Main Authors: Merino, Pedro, Tejero, Tomas
Format: Article
Language:English
Subjects:
aldehydes
asymmetric catalysis
ketones
oxidation
proline
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Summary:The magic of no metal: Enantiomerically pure α‐hydroxy aldehydes and ketones as well as diols can be synthesized by a direct (S)‐proline‐catalyzed asymmetric nitroso‐aldol reaction between the parent carbonyl compound and nitrosobenzene. Further elaboration of the obtained adducts provides useful precursors for diversity‐oriented synthesis. The one‐flask transformation of 3‐phenylpropanal into (R)‐3‐phenylpropane‐1,2‐diol (98 % ee) is one example.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200301760