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Journal Article

Mechanism of the Pummerer Reaction: A Computational Study

MPS-Authors
http://pubman.mpdl.mpg.de/cone/persons/resource/persons58872

Patil,  Mahendra
Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons58774

Loerbroks,  Claudia
Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons59045

Thiel,  Walter
Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Supplementary Material (public)

ol400468z_si_001.pdf
(Supplementary material), 2MB

Citation

Patil, M., Loerbroks, C., & Thiel, W. (2013). Mechanism of the Pummerer Reaction: A Computational Study. Organic Letters, 15(7), 1682-1685. doi:10.1021/ol400468z.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0014-A374-B
Abstract
DFT calculations are used to investigate the mechanism of the Pummerer reaction between a chiral sulfoxide and acetic anhydride under classical and stereoselective reaction conditions (without and with additives, respectively). The first step involving acetylation of the sulfoxide with release of acetate is found to be rate-determining in both cases. For the stereoselective Pummerer reaction in the presence of trimethylsilyl triflate (TMSOTf) and N,N-dimethylacetamide (DMAC), TMSOTf- and DMAC-assisted transition states as well as ion exchange reactions are considered to account for the role of TMSOTf and DMAC.