jo501594g_si_001.pdf (3.44 MB)
Ruthenium-Catalyzed Asymmetric [2 + 2] Cycloadditions between Chiral Acyl Camphorsultam-Substituted Alkynes and Bicyclic Alkenes
journal contribution
posted on 2014-11-07, 00:00 authored by Jordan Goodreid, Karine Villeneuve, Emily Carlson, William TamRuthenium-catalyzed asymmetric [2
+ 2] cycloadditions between chiral
acyl camphorsultam-functionalized alkynes and bicyclic alkenes were
examined, providing adducts with complete exo stereoselectivity
in good overall yield and enantioselectivity (up to 99% and 166:1,
respectively), as well as appreciable diastereoselectivity (up to
163:1). The diastereoselectivity showed dependence on the solvent
and temperature, as well as on the substitution pattern of the reacting
alkyne and bicyclic alkene components. In general, higher diastereoselectivities
were observed for reactions conducted in ethereal solvents and at
lower temperatures between N-propynoyl camphorsultams
and bicyclic alkenes.