Stereocontrolled formation of ketomethylene isosteres through tandem chain extension reactions.
A zinc-mediated chain extension reaction is the key step in the preparation of gamma-keto amides derived from amino acids. The use of tandem reaction sequences, in which the intermediate zinc enolate is trapped with electrophilic reagents, results in the incorporation of alpha-substituents, which mimic the side chains found in natural amino acid systems. Use of the chiral amino acid L-proline as a stereo-directing element provides a diastereoselective route to various ketomethylene isosteres.
Lin
Weimin
W
Department of Chemistry, University of New Hampshire, Durham, New Hampshire 03824, USA.
Tryder
Nancy
N
Su
Fan
F
Zercher
Charles K
CK
Jasinski
Jerry P
JP
Butcher
Ray J
RJ
D007659:Ketones / Q000138:chemical synthesis*
D007659:Ketones