Asymmetric Diels-Alder cycloadditions of D-erythrose 1,3-butadienes to achiral t-butyl 2H-azirine 3-carboxylate

Two D-erythrose 1,3-butadienes were reacted with electrophilic achiral t-butyl 2H-azirine 3-carboxylate giving cycloadducts with good yields and moderate selectivity. The isomers could be separated to give the major (R)-isomers at C-2 in approximately 50% yield in both cases. Alternatively LACASA-DA methodology was applied to one of the reactions leading to homochiral (R)- and (S)-products by changing the chiral nature of an extra chiral BINOL inductor used. (C) 2013 Elsevier Ltd. All rights reserved.