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Diazoacetoacetate enones for the synthesis of diverse natural product-like scaffolds.

ABSTRACT: Diazoacetoacetate enones are a new class of Michael acceptors that enable the efficient construction of natural product-like scaffolds. Through their Michael addition reactions, including those with silyl enol ethers, indoles, pyrroles, and amines, ?-functionalized diazoacetoacetates are formed in high yield and with overall operational efficiency. Subsequent catalytic dinitrogen extrusion reactions provide access to a diverse series of natural product-like carbo- and heterocyclic ring systems in only three steps from commercial materials.

SUBMITTER: Shanahan CS

PROVIDER: S-EPMC3806194 | biostudies-literature | 2013 Jul

REPOSITORIES: biostudies-literature

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Diazoacetoacetate enones for the synthesis of diverse natural product-like scaffolds.

Shanahan Charles S CS Truong Phong P Mason Savannah M SM Leszczynski John S JS Doyle Michael P MP

Organic letters 20130705 14

Diazoacetoacetate enones are a new class of Michael acceptors that enable the efficient construction of natural product-like scaffolds. Through their Michael addition reactions, including those with silyl enol ethers, indoles, pyrroles, and amines, δ-functionalized diazoacetoacetates are formed in high yield and with overall operational efficiency. Subsequent catalytic dinitrogen extrusion reactions provide access to a diverse series of natural product-like carbo- and heterocyclic ring systems i ...[more]

PMID: 23829448

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