☆ 4.4 Article

Cascade cyclization intermolecular dipolar cycloaddition by multi-component couplings - synthesis of indolizidines and pyrrolizidines

TETRAHEDRON LETTERS (2008)

Journal

TETRAHEDRON LETTERS

Volume 49, Issue 37, Pages 5408-5410

Publisher

PERGAMON-ELSEVIER SCIENCE LTD

DOI: 10.1016/j.tetlet.2008.07.010

Keywords

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Categories

Chemistry, Organic

Funding

International Incoming Fellowship [IIF-2007/R1]
EPSRC
AstraZeneca

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Abstract

A three-component coupling reaction of a primary amine (an amino-acid or amino-ester or hydroxylamine), an alkene or alkyne dipolarophile and an aldehyde bearing a halide as a leaving group has been developed. Condensation of the amine with the aldehyde and cyclization (intramolecular N-alkylation) provides, after decarboxylation or deprotonation, a cyclic azomethine ylide (or nitrone) that undergoes intermolecular dipolar cycloaddition with the dipolarophile. This sets up, in a single step, the bicyclic indolizidine or pyrrolizidine ring system, depending on the length of the tether between the aldehyde and the halide. The reaction is successful with stabilized and non-stabilized azomethine ylides that result from using primary amino-esters or amino-acids, respectively. (c) 2008 Elsevier Ltd. All Fights reserved.

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