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Synlett 2006(2): 315-317  
DOI: 10.1055/s-2005-923592
LETTER
© Georg Thieme Verlag Stuttgart · New York

Manganese-Promoted β-Elimination Reactions: Totally Stereoselective Synthesis of (E)-α,β-Unsaturated Esters

José M. Concellón*, Humberto Rodríguez-Solla, Vicente del Amo
Dpto. Química Orgánica e Inorgánica, Universidad de Oviedo, C/ Julián Clavería 8, 33006, Oviedo, Spain
e-Mail: jmcg@fq.uniovi.es;
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Publication History

Received 17 October 2005
Publication Date:
23 December 2005 (online)

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Abstract

Stereoselective β-elimination of 2-bromo-3-hydroxy­esters is achieved by using non-preactivated manganese and tri­methylsilyl chloride, to yield (E)-α,β-unsaturated esters with total diastereoselectivity.

Key words

alkenes - diastereoselectivity - esters - eliminations - manganese

    References and Notes

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4

Aldrich catalogue (2005-2006): manganese (325 mesh): 250 g - 30.50 ı; samarium (40 mesh): 50 g - 325.20 ı; chromium dichloride: 25 g - 541.80 ı.