Addition of 1,3-Benzoxathiole 3-Oxide Anion to Azomethines under Varying Reaction Conditions

CABIDDU S;CADONI, ENZO;IANNI A;GELLI G;MELIS S;BERNARD, ANGELA MARIA;CABIDDU, MARIA GRAZIA;DE MONTIS S;FATTUONI, CLAUDIA

2002-01-01

---

Abstract

The reaction of benzoxathiole 3-oxide with LDA in THF gave an anion which was reacted with azomethines under varying conditions of temperature and solvent. At -78 degreesC in THF, the two diastereomers resulting from a trans addition were mainly obtained, while at temperatures higher than -40 degreesC, or upon increasing the solvent polarity, only one trans and one cis diastereomer were obtained. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.