Diastereoselective Morita-Baylis- Hillman Reaction Using Acrylates Derived from Levoglucosenone

AMARANTE, G. W., SAROTTI, A. M., HORTA, B. A. C., SUÁREZ, A. G., DE ALENCASTRO, R. B., SPANEVELLO, R. A., COELHO, F

Itapema, Brasil

Congreso; 12th Brazilian Meeting on Organic Synthesis.; 2007

Sociedad Brasilera de Química

The development of a general asymmetric version for the MBH reaction continues to attract the attention of research in the whole world. The best results available so far are still limited to the specialized α,β-unsaturated ketones or acrylates.  Levoglucosenone 1 is a versatile member of the carbohydrate-derived chiral pool and it is obtained efficiently by the pyrolysis of cellulose or cellulose-containing material such as waste paper. Spanevello et al. has been introduced successfully the use of 1 as a chiral auxiliary in an asymmetric Diels-Alder reaction. In this communication, we describe the first example of a diastereoselective MBH reaction using acrylates derived from Levoglucosenone.