Sulfur Ylide Chemistry

Graphical Abstract ja-2013-05073w_0001As part of a long-running project in the group of Prof Varinder Aggarwal FRS at the University of Bristol we have been involved in research on the development of chiral sulfur ylides for asymmetric epoxidation, aziridination and epoxidation. A major success story is the development of an easily accessible chiral sulfide which gives high enantioselectivities in epoxidations and aziridinations. isothiocineole TCIThe sulfide can be made from limonene and sulfur in just one step making it cheap to make. It has also become commercially available as a result of our work (TCI cat no T2578 & T2579; Aldrich 766429). We have described its synthesis and application on multi-gram scale.

See: J Am Chem Soc 2013, 135, 11951. DOI: 10.1021/ja405073w

J Am Chem Soc 2010, 132, 1828–1830. DOI: 10.1021/ja9100276

Synthesis 201850, 3337-3343. DOI: 10.1055/s-0037-1609580

We have also worked on improving mechanistic understanding of ylide reactions. Recently isotopic labelling studies revealed how an intramolecular proton transfer was hampering some asymmetric cyclopropanations.

JACS2010 Cycloprop GraphAbstract

See J Am Chem Soc 2010, 132, 7626–7630. DOI: 10.1021/ja910631u

See the publications section for more published papers.