Dave Gorin Seminar "Methylation of Oxygen Nucleophiles with Safe, Stable Methylating Agents."
- 10/25/2013 | 2:45 PM – 3:45 PM
- Location: Druckenmiller Hall, Room 020
- Event Type: Lecture
- Sponsor: Chemistry
- Contact: Penny Westfall
- - Open to the Bowdoin Community -
Dave Gorin of Smith College gives a seminar on "Methylation of Oxygen Nucleophiles with Safe, Stable Methylating Agents."
Although methylation reactions are commonplace, currently used reagents are hazardous, toxic, and/or unstable. Dimethylcarbonate has been put forth as an inexpensive, non-toxic, and "green" potential methylating reagent. We have discovered a general, base-catalyzed methyl transfer from dimethylcarbonate to carboxylic acids. High selectivity for esterification is observed even in the presence of unprotected phenols and the mild reaction conditions enable conservation of stereochemistry at epimerizable stereocenters. Isotope-labeling studies suggest a mechanism proceeding by direct methyl transfer from dimethylcarbonate to the substrate.