New chiral auxiliaries from waste paper

ARIEL M. SAROTTI, ROLANDO A. SPANEVELLO, ALEJANDRA G. SUÁREZ

Canela, Brasil

Simposio; 11th Brazilian Meeting on Organic Synthesis; 2005

Sociedad Brasilera de Química

The generation of useful chemicals from cellulosic waste materials have been investigated through the pyrolysis of acid-pretreated waste paper. Levoglucosenone (1) (1,6-anhydro-3,4-dideoxy-b-D-glycero-hex-3-enopyranos-2-ulose), a bicyclic enone, is the major product obtained from the pyrolysis of cellulose-containing materials. During the last decade this versatile and readily available member of the carbohydrate derived chiral pool, has been intensively used as chiral synthon in the synthesis of a wide variety of natural and unnatural products, some of them showing interesting biological activities. Our interest in this field is focused on the potential use of this chiral building block in the synthesis of asymmetric inductors. This work is the first application of levoglucosenone derivatives as chiral auxiliaries in a Diels-Alder reaction. The level of induction obtained, in addition to the fact that the starting material is inexpensive, makes this system an excellent model to be further exploited in other asymmetric reactions and a starting point for new chiral templates