Models for the use of. alpha.-amino acids as chiral auxiliaries in asymmetric Diels-Alder reactions

MP Bueno, CA Cativiela, JA Mayoral…

Index: Bueno, Maria P.; Cativiela, Carlos A.; Mayoral, Jose A. Journal of Organic Chemistry, 1991 , vol. 56, # 23 p. 6551 - 6555

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Citation Number: 31

Abstract

Three different models, depending on the Lewis acid used as a catalyst and the a-amino acid used as a chiral auxiliary, account for the diastereofacial selectivity obtained in reactions of cyclopentadiene with N-acryloyl derivatives of L-proline, L-phenylalanine, L- alanine, and N-methyl-L-alanine esters. For a-amino acids without an NH group and aluminum catalysts, a reactive conformer with antiplanar enoate conformation similar to ...