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Synlett 2009(3): 390-394  
DOI: 10.1055/s-0028-1087550
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Organocatalytic Synthesis of an Alkyltetrahydropyran

D. Díez*a, M. G. Núñeza, A. Benéiteza, R. F. Moroa, I. S. Marcosa, P. Basabea, H. B. Broughtonb, J. G. Uronesa
a Departamento de Química Orgánica, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, Spain
Fax: +34(923)294574; e-Mail: ddm@usal.es;
b Lilly S. A., Avda de La Industria 30, 28108 Alcobendas, Madrid, Spain
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Publikationsverlauf

Received 2 September 2008
Publikationsdatum:
21. Januar 2009 (online)

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Abstract

The first synthesis of an alkyltetrahydropyran using a ­diarylprolinol organocatalyst is described.

Keywords

organocatalysis - tetrahydropyrans - diarylprolinol - ­cyclization

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29

When reductions were performed with NaBH4, MeOH was added as cosolvent.

30

A racemic mixture of compound 16 was obtained by iodine cyclization of compound 13 and subsequent NaBH4 reduction of the iodo derivatives obtained.

32

See the Supporting Information available.