A Convergent Route to b-Amino Acids and to b-Heteroarylethylamines. An Unexpected Vinylation Reaction

Xuan Chen (1) , Samir Z Zard (1)

1 DCSO - Laboratoire de synthèse organique

Various protected β2-amino acids can be prepared by radical addition of β-phthalimido-α-xanthyl propionic acid, both as the free acid or as the ethyl ester. Successive radical additions provide access to more complex structures. In the case of the free acid, addition to certain heteroaromatics leads directly to β-heteroarylethylamines through spontaneous decarboxylation of the intermediate adduct. Forcing the decarboxylation in some cases generated a vinyl group by decarboxylative elimination of the phthalimido group.

Domaines: Chimie organique

Xuan Chen, Samir Z Zard. A Convergent Route to b-Amino Acids and to b-Heteroarylethylamines. An Unexpected Vinylation Reaction. Organic Letters, 2020, 22 (9), pp.3628-3632. ⟨10.1021/acs.orglett.0c01087⟩. ⟨hal-03416909⟩