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Tandem Chain Extension-Iodomethylation Reactions: Formation of alpha-Functionalized gamma-Keto Carbonyls.

ABSTRACT: 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.

SUBMITTER: Pu Q

PROVIDER: S-EPMC2598404 | biostudies-literature | 2008 Aug

REPOSITORIES: biostudies-literature

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Tandem Chain Extension-Iodomethylation Reactions: Formation of alpha-Functionalized gamma-Keto Carbonyls.

Pu Qinglin Q Wilson Emerald E Zercher Charles K CK

Tetrahedron 20080801 35

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. ...[more]

PMID: 19710906

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