Tandem Chain Extension–Iodomethylation Reactions: Formation of α-Functionalized γ-Keto Carbonyls
Sequential exposure of a zinc-organometallic intermediate, generated through a zinc carbenoid-mediated chain extension reaction of a β-keto carbonyl, to trimethylsilylchloride and iodine provided regioselective formation of an α-iodomethyl-γ-keto carbonyl. The iodomethyl functionality can be further manipulated to provide side chains that are potential mimics of α-amino acid side chains.
Digital Object Identifier (DOI)
Tandem Chain Extension–Iodomethylation Reactions: Formation of α-Functionalized γ-Keto Carbonyls, Pu, Q.; Wilson, E.; Zercher, C. K. Tetrahedron 2008, 64, 8045-8051.
Copyright © 2008, Elsevier