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Organocatalyzed Asymmetric α‐Aminoxylation of Aldehydes and Ketones—An Efficient Access to Enantiomerically Pure α‐Hydroxycarbonyl Compounds, Diols, and Even Amino Alcohols
Author(s) -
Merino Pedro,
Tejero Tomas
Publication year - 2004
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200301760
Subject(s) - nitrosobenzene , chemistry , aldol reaction , adduct , organic chemistry , nitroso , diol , catalysis , alcohol
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.