Jeffery Richardson

TL;DR: A general process for the in situ generation of diazo compounds from tosylhydrazone sodium salts has been established and applied in sulfur-ylide mediated epoxidation reactions and a general rationalization of the factors that influence both relative and absolute stereochemistry for all of the different substrates is provided.

TL;DR: It is shown that E/Z selectivity of non- and semi-stabilized ylides cannot be fully understood without considering the energy of the elimination TS, and the influence of ylide stabilization and the nature of phosphorus substituents on reversibility of oxaphosphetane formation is clarified.

TL;DR: A novel picture of the mechanism provides a sound basis for the future development of chiral sulfides for enantioselective epoxide synthesis.

TL;DR: Factors that influence the degree of reversibility in betaine formation are critically important since with subtle changes in reaction conditions both high enantio- and diastereoselectivity can often be achieved.

TL;DR: A practical, catalytic, and asymmetric conversion of aldehydes into epoxides by using the sulfide 1 (Scheme 1) is reported, obtained in four steps in 48% overall yield from camphorsulfonyl chloride.