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Pure Appl. Chem., 2013, Vol. 85, No. 8, pp. 1683-1692

Published online 2013-07-10

Cellulose recycling as a source of raw chirality

Valeria Corne, María Celeste Botta, Enrique D. V. Giordano, Germán F. Giri, David F. Llompart, Hernán D. Biava, Ariel M. Sarotti, María I. Mangione, Ernesto G. Mata, Alejandra G. Suárez and Rolando A. Spanevello*

Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario – CONICET, Suipacha 531, S2002LRK, Rosario, Argentina

Abstract: Modern organic chemistry requires easily obtainable chiral building blocks that show high chemical versatility for their application in the synthesis of enantiopure compounds. Biomass has been demonstrated to be a widely available raw material that represents the only abundant source of renewable organic carbon. Through the pyrolitic conversion of cellulose or cellulose-containing materials it is possible to produce levoglucosenone, a highly functionalized chiral structure. This compound has been innovatively used as a template for the synthesis of key intermediates of biologically active products and for the preparation of chiral auxiliaries, catalysts, and organocatalysts for their application in asymmetric synthesis.