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DTBB-Catalysed Lithiation of Cis- and Trans-2,3-diphenyloxirane Gives the Same Organolithium Intermediate
1 , 2 , 2 , 1 , * 2
1  Departamento de Química Inorgánica, Instituto de Ciencias de los Materiales de Aragón, Facultad de Ciencias, Universidad de Zaragoza-CSIC, 5009 Zaragoza, Spain
2  Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain

Abstract: The reaction of cis- or trans-2,3-diphenyloxirane with lithium powder and a catalytic amount of 4,4’-di-tert-butylbiphenyl (DTBB, 5% molar) in the presence of 3-pentanone as electrophile in THF at temperatures ranging between –90 and –50ºC gives, after hydrolysis with water, the corresponding 1,3-diol 5 with the same stereochemistry (1S*,2R*) independently of the geometry of the starting oxiranes. A mechanistic explanation for this behaviour is given.
Keywords: DTBB-catalysed lithiation; reductive opening of oxiranes