Fig. 4: Gram-scale reaction and transformations of the nitro group. | Nature Communications

Fig. 4: Gram-scale reaction and transformations of the nitro group.

From: Synthesis of chiral anti-1,2-diamine derivatives through copper(I)-catalyzed asymmetric α-addition of ketimines to aldimines

Fig. 4

a Gram-scale reaction. b Transformation of the nitro group to the nitrone group. Zn (6.0 equiv), HOAc (12.0 equiv), EtOH, 0 °C to RT. c Removal of the ketimine moiety and protection of the newly generated free amine moiety. (1) 12 M HCl, MeOH, RT; (2) TsCl, Et3N, DMAP, DCM, RT. d Reduction of the nitro group to the amine group. Pd/C, H2 (1 atm), MeOH, RT. e Radical hydroamination. (1) 3-methylbut-3-en-1-ol (3.0 equiv), Fe(acac)3 (30 mol %), PhSiH3, EtOH, 60 °C; (2) Zn, HCl, 60 °C.

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