Tandem chain extension-iodomethylation reactions: formation of α-functionalized γ-keto carbonyls

DOI: 10.1016/j.tet.2008.06.063

Source and publish data:

Tetrahedron p. 8045 - 8051 (2008)

Update date:2022-07-29

Topics:

Authors:

Pu, Qinglin

Wilson, Emerald

Zercher, Charles K.

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Article abstract of DOI:10.1016/j.tet.2008.06.063

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.

Full text of DOI:10.1016/j.tet.2008.06.063

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