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Design of a bisamidinium claisen rearrangement catalyst for monodentate substrates.

ABSTRACT: A bisamidinium catalyst has been designed for the Claisen rearrangement. The primary design feature is a dual hydrogen bonding array that can coordinate a singular oxygen atom of the substrate. The ability to function as a dual hydrogen donor is key as the bisamidinium accelerates the Claisen rearrangement to a greater extent than Brønsted acids with lower pK(a) values.

SUBMITTER: Annamalai VR

PROVIDER: S-EPMC2653207 | biostudies-literature | 2009 Feb

REPOSITORIES: biostudies-literature

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Design of a bisamidinium claisen rearrangement catalyst for monodentate substrates.

Annamalai Venkatachalam R VR Linton Elizabeth C EC Kozlowski Marisa C MC

Organic letters 20090201 3

A bisamidinium catalyst has been designed for the Claisen rearrangement. The primary design feature is a dual hydrogen bonding array that can coordinate a singular oxygen atom of the substrate. The ability to function as a dual hydrogen donor is key as the bisamidinium accelerates the Claisen rearrangement to a greater extent than Brønsted acids with lower pK(a) values. ...[more]

PMID: 19175347

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