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Diastereoselective synthesis of 3,6-disubstituted 3,6-dihydropyridin-2-ones

Lookup NU author(s): Mr TF Anderson Anderson, Dr Julian Knight, Dr Kirill Tchabanenko

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Abstract

In a short sequence, 5-vinyloxazolidin-2-ones were converted into the 3,6-disubstituted 3,6-dihydropyridin-2-ones via Pd-catalysed carbonylation and enolate alkylation with high diastereoselectivity. Alkylation of 6-substituted N-methylpyridin-2-ones gives stereoselectively the 3,6-anti diastereoisomer with MeI, BuI and i-PrI. Alkylation of the corresponding N-BOC pyridinones gives the 3,6-syn diastereoisomer with high selectivity. © 2003 Elsevier Science Ltd. All rights reserved.

Publication metadata

Author(s): Anderson TF, Knight JG, Tchabanenko K

Publication type: Article

Publication status: Published

Journal: Tetrahedron Letters

Year: 2003

Volume: 44

Issue: 4

Pages: 757-760

ISSN (print): 0040-4039

ISSN (electronic): 1873-3581

Publisher: Pergamon

URL: http://dx.doi.org/10.1016/S0040-4039(02)02677-1

DOI: 10.1016/S0040-4039(02)02677-1

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