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Mechanism of the Pummerer Reaction: A Computational Study

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

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

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

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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: https://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.