Title

Tandem Chain Extension–Iodomethylation Reactions: Formation of α-Functionalized γ-Keto Carbonyls

Abstract

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.

Publication Date

8-25-2008

Journal Title

Tetrahedron

Publisher

Elsevier

Digital Object Identifier (DOI)

10.1016/j.tet.2008.06.063

Document Type

Article

Rights

Copyright © 2008, Elsevier