Stereoselective syntheses of trisubstituted olefins via platinum catalysis: alpha-silylenones with geometrical complementarity.
The stereoselective syntheses of alpha-silylenones using catalytic PtCl(2) are reported. Via alkyne activation, alpha-hydroxypropargylsilanes are converted to (Z)-silylenones through a highly selective silicon migration. The complementary (E)-silylenones are accessed by a regioselective hydrosilylation of the ynone precursor. The synthetic utility of these compounds is demonstrated in cross-coupling reactions, highlighting the potential of these protocols for the syntheses of geometrically defined trisubstituted olefins.
Rooke
Douglas A
DA
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
Ferreira
Eric M
EM
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D010984:Platinum / Q000737:chemistry*; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D000480:Alkynes; D012821:Silanes; D010984:Platinum