Events The 8th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

10.3390/ecsoc-8-01936

This submission belongs to the session a. General Organic Synthesis of the event The 8th International Electronic Conference on Synthetic Organic Chemistry

Published date

01 Nov, 2004

Citation

Larry R. Falvello, Cecilia Gómez, Beatriz Maciá, Tatiana Soler, Miguel Yus, DTBB-Catalysed Lithiation of Cis- and Trans-2,3-diphenyloxirane Gives the Same Organolithium Intermediate, in Proceedings of The 8th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2004, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-8-01936

Facebook

Twitter

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

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

Deprotection of N-Pivaloylindoles, Carbazoles and Beta-Carbolines with a Lithium Base

Enantiospecific Preparation of 10-(pyperidin-1-yl)Camphor: A Model Procedure for 10-Aminocamphors