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Synlett 2011(14): 2059-2063  
DOI: 10.1055/s-0030-1261161
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Heck Reaction on Morita-Baylis-Hillman Adducts: Diastereoselective Synthesis of Pyrrolizidinones and Pyrrolizidines

Kristerson R. de Luna Freire, Cláudio F. Tormena, Fernando Coelho*
Universidade de Campinas, UNICAMP, Instituto de Química, Departamento de Química Orgânica, Caixa Postal 6154,13083-970 Campinas, SP, Brazil
Fax: +55(19)35213023; e-Mail: coelho@iqm.unicamp.br;
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Publication History

Received 1 March 2011
Publication Date:
10 August 2011 (online)

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Abstract

An efficient approach to the diastereoselective synthesis of benzylidene-, benzyl-pyrrolizidinones, and pyrrolizidines is described. The sequence is based on a highly stereoselective Heck ­reaction between a hydroxylated pyrrolizidinone, prepared from a Morita-Baylis-Hillman adduct, and a suitable aryl halide, using Nájera’s oxime derived palladacycle as catalyst.

Key words

Morita-Baylis-Hillman - Heck reaction - bicyclic compounds - heterocycles - palladium