DTBB-Catalysed Lithiation of Cis- and Trans-2,3-diphenyloxirane Gives the Same Organolithium Intermediate

Larry Falvello; Cecilia Gómez; Beatriz Maciá; Tatiana Soler; Miguel Yus

doi:10.3390/ecsoc-8-01936

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DTBB-Catalysed Lithiation of Cis- and Trans-2,3-diphenyloxirane Gives the Same Organolithium Intermediate

Larry R. Falvello

¹,

Cecilia Gómez

²,

Beatriz Maciá

²,

Tatiana Soler

¹,

Miguel Yus

^{*

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

Published: 01 November 2004 by MDPI in The 8th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-8-01936

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

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Larry Falvello

Cecilia Gómez

Beatriz Maciá

Tatiana Soler

Miguel Yus