Previous Article in event
Next Article in event
DTBB-Catalysed Lithiation of Cis- and Trans-2,3-diphenyloxirane Gives the Same Organolithium Intermediate
Published: 01 November 2004 by MDPI in The 8th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis
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