TY - JOUR A1 - Pereira, Vera Lúcia Patrocinio A1 - Moura, André Luiz da Silva A1 - Vieira, Daniel Pais Pires A1 - de Carvalho, Leandro Lara A1 - Torres, Eliz Regina Bueno A1 - Costa, Jeronimo da Silva T1 - A versatile and efficient approach for the synthesis of chiral 1,3-nitroamines and 1,3-diamines via conjugate addition to new (S,E)-γ-aminated nitroalkenes derived from L-α-amino acids JF - Beilstein Journal of Organic Chemistry PY - 2013/// VL - 9 SP - 832 EP - 837 SN - 1860-5397 DO - 10.3762/bjoc.9.95 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.9.95 KW - amino alcohol KW - amino aldehyde KW - azide addition KW - Baylis–Hillman reaction KW - cyanide addition KW - Michael addition N2 - New chiral (S,E)-γ-N,N-dibenzylated nitroalkenes 2a–c were synthesized from natural L-(α)-amino acids in five steps with overall yields of 68–88%. The conjugate addition of hydride, methoxide, nitronate and azide nucleophiles to 2a–c led to the corresponding chiral 1,3-nitroamines in 74–90% yield. The conjugate addition of cyanide anion to 2a,b was followed by HNO2 elimination affording chiral aminated acrylonitriles (73–98%). On the other hand, the azide anion reacted with 2a, in acetonitrile, via a [3 + 2]-cycloaddition in which HNO2 was lost, providing the corresponding 1,2,3-triazole derivative. Direct reduction of 1,3-nitroamine derivatives 9a,b produced the corresponding 1,3-diamines in good yields. ER -