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

GIOVANNI W. AMARANTE; ARIEL M. SAROTTI; BRUNO A. C. HORTA; ALEJADRA G. SUÁREZ; RICARDO B. DE ALENCASTRO; ROLANDO A. SPANEVELLO; FERNANDO COELHO

Itapema, Brasil

Congreso; 12th Brazilian Meeting on Organic Synthesis; 2007

The development of a general asymmetric version for the MBH 1 reaction continues to attract theattention of research in the whole world. The best results available so far are still limited to the specialized a ,b -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.