Tandem Chain Extension-Iodomethylation Reactions: Formation of alpha-Functionalized gamma-Keto Carbonyls.
Sequential exposure of a zinc-organometallic intermediate, generated through a zinc carbenoid-mediated chain extension reaction of a beta-keto carbonyl, to trimethylsilylchloride and iodine provided regioselective formation of an alpha-iodomethyl-gamma-keto carbonyl. The iodomethyl functionality can be further manipulated to provide side chains that are potential mimics of alpha-amino acid side chains.
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Qinglin
Q
Department of Chemistry, University of New Hampshire, Durham, NH 03824.
Wilson
Emerald
E
Zercher
Charles K
CK