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Cover Picture: Catalytic Enantioselective Tautomerization of Isolated Enols (Angew. Chem. Int. Ed. 37/2007)
Author(s) -
Fehr Charles
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200790181
Subject(s) - enantioselective synthesis , tautomer , enol , chemistry , stereochemistry , lithium (medication) , cover (algebra) , stereoselectivity , catalysis , organic chemistry , psychology , mechanical engineering , engineering , psychiatry
The stereoselective formation and isolation of E enolates can be achieved either from the lithium enolate and isopropylephedrine or from the enol and lithium isopropylephedrate. As shown by C. Fehr on page 7119 ff., both pathways lead to the appreciated fragrance compound ( S )‐α‐damascone which, as suggested by the cover picture, is chiral and smells rosy. The nonlinear effects observed by using a non‐enantiomerically rich isopropylephedrine suggest that higher order mixed aggregates are involved in the enantioselective enol tautomerization. (B. Cogerino is thanked for the photo and Dr. A. Herrmann is thanked for assistance with the layout.)