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Synthesis 2001(7): 1069-1075
DOI: 10.1055/s-2001-14905
PAPER
© Georg Thieme Verlag Stuttgart · New York

On the Stereoselectivity of the Synthesis of 1-Hydroxymethyl-4-phenylsulfonylbuta-1,3-dienes from β,γ-Unsaturated Sulfones

David Díez Martin*, Sonia G. San Feliciano, Isidro S. Marcos, Pilar Basabe, Narciso M. Garrido, Julio G. Urones
Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad de Salamanca, 37008 Salamanca, Spain
Fax: +34(92)3294574; e-Mail: ddm@gugu.usal.es;
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Publication History

Received 12 January 2001
Publication Date:
30 September 2004 (online)

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Abstract

Starting from D-mannitol, eight β,γ-unsaturated sulfones with different substitution patterns have been synthesised. Reaction of these sulfones with different bases led to 1-hydroxymethyl-4-phenylsulfonylbuta-1,3-dienes with excellent stereocontrol. The stereoselectivity of this reaction is explained and an abbreviated reaction course is proposed that justifies the results obtained.

Key words

sulfone - diene - stereoselectivity - synthesis

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