Tetrahedron letters

Anionic cyclizations of aromatic ester dithioacetals with facially biased α, β-unsaturated ketones

CF Morrison, CTM Stamp, DJ Burnell

Index: Morrison, Christopher F.; Stamp, Craig T.M.; Burnell, D. Jean Tetrahedron Letters, 2009 , vol. 50, # 50 p. 7021 - 7023

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Citation Number: 4

Abstract

Cyclopent-2-enones bearing a plane-nonsymmetric oxygen function on C-4 reacted efficiently with anions derived from aromatic ester dithioacetals to provide annulated products in a highly diastereoselective fashion. Whereas the anion of a dimethoxy aromatic ester dithiolane more rapidly reacted by an alternative intramolecular pathway, the anion of the corresponding aromatic ester dithiane was suitable for the intermolecular cyclization.