Mild metal-free syn-stereoselective ring opening of activated epoxides and aziridines with aryl borates

M Pineschi, F Bertolini, RM Haak, P Crotti…

Index: Pineschi, Mauro; Bertolini, Ferruccio; Haak, Robert M.; Crotti, Paolo; Macchia, Franco Chemical Communications, 2005 , # 11 p. 1426 - 1428

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Citation Number: 17

Abstract

The introduction of an electron-withdrawing group at the β-carbon is known to retard the isomerization to carbonyl compounds. 11 In this respect, trans aryl glycidic esters, easily accessible by Darzen reaction, attracted our attention. As shown in entry 7, the ring opening of a glycidic ester with catechol under neutral conditions occurred with complete regio- and high syn-stereoselectivity, giving the corresponding hydroxy phenol 8 with good yield and ...