Events The 14th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

This submission belongs to the session a. General Organic Synthesis of the event The 14th International Electronic Conference on Synthetic Organic Chemistry

Published date

22 Oct, 2010

Citation

Julio C. Podestá, Liliana C. Koll, Flavia C. Zacconi, Synthesis of Optically Active Derivatives of Bicyclic Chiral Diols with C₂ Symmetry, in Proceedings of The 14th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2010, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-14-00382

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Synthesis of Optically Active Derivatives of Bicyclic Chiral Diols with C₂ Symmetry

Julio C. Podestá ¹

Liliana C. Koll ¹

Flavia C. Zacconi ¹

1. Departamento de Química and INQUISUR (UNS-CONICET), Universidad Nacional del Sur, Avda. Alem 1253, 8000 Bahía Blanca, Argentina

Abstract

Efficient synthesis, besides other, of dibromide, diazide, diamine and diesters derived from (11R,12R)-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol (3), a chiral bicyclic diol with C₂ symmetry, was developed. Esterification of 3 with saturated and unsaturated carboxylic acids and acids chlorides leads to the corresponding normal-, olefinic- and acetylenic diesters in average yields of 81%. Also more efficient techniques for the preparation of starting diol 3 in higher yields as well as for a very simple separation of DCU from reactions carried out following DCC/DMAP mehod are described.

Keywords

C2 symmetry

9,10-dihydro-9,10-ethanoanthracene

chiral ligands

Synthesis of Conformationally Restricted Glycoamino Acids using Fluorinating Agents

Synthesis of New Homologous Series of Schiff Base Liquid Crystals with Iodo Terminal Group

Synthesis of Optically Active Derivatives of Bicyclic Chiral Diols with C2 Symmetry

Synthesis of Optically Active Derivatives of Bicyclic Chiral Diols with C₂ Symmetry