17694-78-9Relevant articles and documents
Explorations into the potential of chiral sulfonium reagents to effect asymmetric halonium additions to isolated alkenes
Brucks, Alexandria P.,Treitler, Daniel S.,Liu, Shu-An,Snyder, Scott A.
, p. 1886 - 1898 (2013/07/26)
While methods for the racemic dihalogenation and halohydroxylation of alkenes have been known for decades, enantioselective variants of these processes remain elusive. Initial attempts were made to overcome this long-standing challenge by exploring the potential of chiral, crystalline, sulfur-derived halonium reagents to accomplish the asymmetric dichlorination and iodohydroxylation of 1,2-dihydronaphthalene. Asymmetric dichlorination of this substrate was achieved in 57% yield and 14% enantiomeric excess (ee), but asymmetric iodohydroxylation was much more successful, giving 67% yield and 63% ee. Thorough studies were made of these processes, including investigation of various chiral sulfide derivatives, their substrate scopes, and the reaction conditions. Georg Thieme Verlag Stuttgart · New York.