Selective Michael-aldol reaction by use of sterically hindered aluminum aryloxides as Lewis acids: an easy approach to cyclobutane amino acids |
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Authors: | Avenoza Alberto Busto Jesús H Canal Noelia Peregrina Jesús M Pérez-Fernández Marta |
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Affiliation: | Universidad de La Rioja, Departamento de Química, UA-CSIC E-26006 Logro?o, Spain. alberto.avenoza@dq.uniroija.es |
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Abstract: | A formal [2 + 2] cycloaddition of 2-amidoacrylates with monosubstituted donor olefins, including its asymmetric version, is described. The stereoselectivity of this reaction can be modulated by the use of sterically hindered aluminum aryloxides or methylaluminoxane as Lewis acids. The reaction was applied to the synthesis of both stereoisomers of 2-benzyloxycyclobutane-alpha-amino acid, which are protected serine analogues c(4)Ser(OBn). |
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