Exploring Structural Effects of Biomass Derived Chiral Auxiliaries in Highly Asymmetric Diels-Alder Reactions

SAROTTI, A. M, SUÁREZ, A. G., SPANEVELLO, R. A

Itapema, Brasil.

Congreso; 12th Brazilian Meeting on Organic Synthesis; 2007

Sociedad Brasilera de Química

As part of our program on the pyrolytic conversion of biomass into high value chemicals, we have been concerned with the synthetic application of levoglucosenone as chiral building block in the development of new tools for asymmetric synthesis. Recently, we have reported the synthesis of several chiral auxiliaries derived from this bicyclic enone, which have been used as a chiral template in an asymmetric Diels-Alder reaction. In this study we report the synthesis and evaluation of new chiral auxiliaries substituted at the benzylic position.