Alkene selenenylation: A comprehensive analysis of relative reactivities, stereochemistry and asymmetric induction, and their comparisons with sulfenylation

• Vadim A. Soloshonok and
• Donna J. Nelson

Beilstein J. Org. Chem. 2011, 7, 744–758, doi:10.3762/bjoc.7.85

• Institute of Technology, Cambridge, MA 02139 10.3762/bjoc.7.85 Abstract A broad perspective of various factors influencing alkene selenenylation has been developed by concurrent detailed analysis of key experimental and theoretical data, such as asymmetric induction, stereochemistry, relative reactivities

• to entries in Table 1. Structure of intermediate complex 9. Plot of log krel values for PhSCl addition to alkenes versus their IEs. Data are from Table 6. Plausible mechanism of alkene selenenylation. Major products from reactions of 1 and 2 with representative alkenols. Representative alkene IEs (eV

• the degree of substitution on C=C or upon substituent electronic effects. Electronic and steric effects influencing asymmetric induction, stereochemistry, regiochemistry, and relative reactivities in the addition of PhSeOTf to alkenes are compared and contrasted with those of PhSCl. Keywords: alkene