Synlett 2006(6): 939-941  
DOI: 10.1055/s-2006-933141
LETTER
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Synthesis of cis-3-Oxy-2,2,6,6-tetrasubstituted Tetrahydropyrans

David Díez*, Marta G. Núñez, R. F. Moro, W. Lumeras, Isidro S. Marcos, P. Basabe, Julio G. Urones
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;
Further Information

Publication History

Received 30 November 2005
Publication Date:
14 March 2006 (online)

Abstract

A synthesis of cis-3-oxy-2,2,6,6-tetrasubstituted tetrahydropyrans has been achieved in an easy and straightforward way.

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Spectroscopic Data for Compound 12.
[α]D 20 +22.5 (c 1.0, CHCl3). IR (film): 3460 (br), 2970-2870, 1454, 1377, 1221, 1069, 974, 731, 696 cm-1. 1H NMR (400 MHz, CDCl3): δ = 7.46-7.30 (5 H, m, Ph), 4.85 (1 H, dd, J = 3.4, 10.1 Hz, H-1′), 4.58 (1 H, d, J = 10.8 Hz, OCH2Ph, HA), 4.48 (1 H, d, J = 10.8 Hz, OCH2Ph, HB), 4.09 (1 H, m, HA-2′), 3.94 (1 H, m, HB-2′), 3.43 (1 H, m, H-3), 2.05-1.85 (4 H, m, H-4, H-5), 1.51 (3 H, s, H-9), 1.26, 1.22 (3 H each, s, H-7 and H-8) ppm. 13C NMR (100 MHz, CDCl3): δ = 18.33 (C-4), 20.13 (C-9), 27.44 (C-7), 29.34 (C-5), 32.81 (C-8), 39.12 (C-1′), 66.70 (C-2′), 71.15 (PhCH2), 74.04 (C-6), 75.98 (C-3), 127.47 (Ph para ), 127.69 (Ph ortho ), 128.25 (Ph meta ), 138.45 (Ph ipso ) ppm. HMRS (EI): m/z calcd for C17H26O3I: 405.0927 [M + H]+; found: 405.0944.