Issue 2, 1997

Formation and X-ray structural study of enantiopure fused 1,5-oxathiocane derivatives

Abstract

The reaction of (E,RS)-3-[(1S)-isoborneol-10-sulf inyl]-1-methoxybuta-1,3-diene 1 with benzaldehyde or p-nitrobenzaldehyde, when carried out in dichloromethane in the presence of trimethylsilyl trifluoromethanesulfonate, leads mainly to enantiopure condensed 2-aryl-4-ethylidene-1,5-oxathiocane S-oxides. The reaction path begins with the ionic addition of the enantiopure diene 1 onto the C[double bond, length as m-dash]O group activated by trimethylsilyl cation attack on the carbonyl oxygen. The almost complete diastereoselection observed in the following closure of the eight-membered ring is interpreted as being a consequence of the conformational control on cyclization which leads to the thermodynamically favoured isomer. The crystal structure of the 2,4-dinitrophenylhydrazone of the α,β-unsaturated aldehyde 5, obtained by reacting diene 1 with p-nitrobenzaldeyde, supports the stereochemical results.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1997, 273-278

Formation and X-ray structural study of enantiopure fused 1,5-oxathiocane derivatives

M. C. Aversa, A. Barattucci, P. Bonaccorsi, G. Bruno, P. Giannetto and F. Nicolò, J. Chem. Soc., Perkin Trans. 2, 1997, 273 DOI: 10.1039/A604910I

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