Asymmetric Diels–Alder cycloadditions of d-erythrose 1,3-butadienes to achiral t-butyl 2H-azirine 3-carboxylate |
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Authors: | Vera CM Duarte Hélio Faustino Maria J Alves António Gil Fortes Nuno Micaelo |
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Institution: | Departamento de Química, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal |
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Abstract: | 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. |
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