Application of the Z-selective Still–Gennari modification of Horner–Wadsworth–Emmons
(HWE) reaction for the olefination of acylphosphonates is presented. A series of new
Z-α,β-unsaturated phosphonates containing a carbonyl or ester moiety in the β-position
were obtained in up to 94% yield and with up to 96% Z-selectivity. The standard HWE olefination of the acylphosphonates, which was performed
for comparison, was either unsuccessful at all, or resulted in an inferior Z-selectivity and lower isolated yields.
Key words
Still–Gennari olefination -
Z-selective Horner–Wadsworth–Emmons reaction - α,β-unsaturated phosphonates - vinylphosphonates
