Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 348, Issue 7-8, Pages 826-832Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200505443
Keywords
asymmetric catalysis; bifunctional organocatalysts; DFT calculations; Michael addition; transition states
Categories
Ask authors/readers for more resources
A highly enantioselective (84-92% ee) organocatalytic Michael addition of acetone to aromatic nitroolefins has been described. The transition state geometries for formation of R and S enantiomers in this Michael addition have been calculated and analyzed. It was shown that only one oxygen atom of the nitro group is bound to the thiourea moiety, in juxtaposition to the working hypothesis known from the literature which involves a bonding of both oxygens. The theoretical and experimental enantiomeric excess values show good agreement, rendering the computations an efficient tool for predicting the ee values in similar reactions.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available