54.An Unprecedented Silver Salt Effect Switches the Facial Selectivity in the Vinylogous Mukaiyama Aldol Reaction

Y. Liang, L. Wang, R. Zhu, L. J. Deng, Y. Yang, J. M. Quan, J. H. Chen*, Z. Yang*

Adv. Synth. Catal. 2010, 352, 2387.

Silver hexafluroantimonate was identified as a highly efficient agent to reverse the facial selectivity of the titanium chloride-mediated vinylogous Mukaiyama aldol reaction (VMAR), and this unprecedented reaction provides a concise, diastereoselective synthesis of δ-hydroxy-α,γ-dimethyl-α,β-unsaturated carbonyl units from readily available chiral vinylketene silyl N,O-acetal 6 and ethyl glyoxylate 8.