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2005
Enantioselective syntheses
O 0031
Catalytic Enantioselective Construction of All-Carbon Quaternary Stereocenters:
and Mechanistic Studies of the C-Acylation of Silyl Ketene Acetals. —
35- 031 Synthetic
Reaction of acyclic silyl ketene acetals, e.g. (I), with acetic anhydride proceeds smoothly in the presence of an axially chiral ferrocene catalyst (PPY) to afford β-oxocarboxylic acid esters, e.g. (III), in good yields and high enantioselectivities. Interestingly,
both geometrical isomers of the silyl ketene acetals react to give the same enantiomer
of the product. — (MERMERIAN, A. H.; FU*, G. C.; J. Am. Chem. Soc. 127 (2005)
15, 5604-5607; Dep. Chem., MIT, Cambridge, MA 02139, USA; Eng.) — Mischke
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