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

• Vera Lúcia Patrocinio Pereira,
• André Luiz da Silva Moura,
• Daniel Pais Pires Vieira,
• Leandro Lara de Carvalho,
• Eliz Regina Bueno Torres and
• Jeronimo da Silva Costa

Beilstein J. Org. Chem. 2013, 9, 832–837, doi:10.3762/bjoc.9.95

• alcohol; amino aldehyde; azide addition; Baylis–Hillman reaction; cyanide addition; Michael addition; Introduction Nitroalkenes constitute a class of organic compounds that present exceptional versatility in organic synthesis [1][2][3][4]. They are reactive in Michael reactions with a wide variety of

• reaction times were employed (Table 1, entries 4 and 5). On the other hand, a severe decrease in the diastereoselectivity occurred with longer durations, presumably due to an equilibration by a retro-conjugate addition [77] (Table 1, entries 6–8). Next, the conjugate cyanide addition to 2a,b promoted by

• addition of “HCN” equivalent to nitroalkenes is rare in the literature [78][79][80][81][82][83]. Paulsen [78] and Sakakibara [79] were the first authors to report the cyanide addition to α,β-unsaturated nitroalkenes. In agreement with our results, Sakakibara [79] and Spanevello [80] observed a total or