A generic and reproducible route to homo- and heteroannular bicyclic beta-diketones via knochel-type 1,4-conjugate additions to alpha,beta-unsaturated cycloalkenones

C L  Hill; M  McGrath; T  Hunt; G  Grogan

doi:10.1055/s-2005-923581

A generic and reproducible route to homo- and heteroannular bicyclic beta-diketones via knochel-type 1,4-conjugate additions to alpha,beta-unsaturated cycloalkenones

C L Hill, M McGrath, T Hunt, G Grogan

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

A generic and reproducible method for the preparation of homo- and heteroannular bicyclic beta-diketones is reported. The method employs the copper acetate mediated 1,4-conjugate addition of organozinc derivatives of iodopropionate and iodobutanoate esters to alpha, beta-unsaturated cycloalkenones, followed by intramolecular Dieckmann condensation.

Original language	English
Pages (from-to)	309-311
Number of pages	3
Journal	Synlett
Issue number	2
DOIs	https://doi.org/10.1055/s-2005-923581
Publication status	Published - 1 Feb 2006

Keywords

annulation
enzymes
bicyclic compounds
ketones
cyclisations
1,3-DIKETONES
REAGENTS

Access to Document

10.1055/s-2005-923581

Cite this

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abstract = "A generic and reproducible method for the preparation of homo- and heteroannular bicyclic beta-diketones is reported. The method employs the copper acetate mediated 1,4-conjugate addition of organozinc derivatives of iodopropionate and iodobutanoate esters to alpha, beta-unsaturated cycloalkenones, followed by intramolecular Dieckmann condensation.",

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AU - McGrath, M

AU - Hunt, T

AU - Grogan, G

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N2 - A generic and reproducible method for the preparation of homo- and heteroannular bicyclic beta-diketones is reported. The method employs the copper acetate mediated 1,4-conjugate addition of organozinc derivatives of iodopropionate and iodobutanoate esters to alpha, beta-unsaturated cycloalkenones, followed by intramolecular Dieckmann condensation.

AB - A generic and reproducible method for the preparation of homo- and heteroannular bicyclic beta-diketones is reported. The method employs the copper acetate mediated 1,4-conjugate addition of organozinc derivatives of iodopropionate and iodobutanoate esters to alpha, beta-unsaturated cycloalkenones, followed by intramolecular Dieckmann condensation.

KW - annulation

KW - enzymes

KW - bicyclic compounds

KW - ketones

KW - cyclisations

KW - 1,3-DIKETONES

KW - REAGENTS

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DO - 10.1055/s-2005-923581

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