Asymmetric synthesis of β-amino cyanoesters with contiguous tetrasubstituted carbon centers by halogen-bonding catalysis with chiral halonium salt

• Yasushi Yoshida,
• Maho Aono,
• Takashi Mino and
• Masami Sakamoto

Beilstein J. Org. Chem. 2025, 21, 547–555, doi:10.3762/bjoc.21.43

• , which formed the corresponding products in high to excellent enantioselectivities. In this paper, the asymmetric synthesis of β-amino cyanoesters with contiguous tetrasubstituted carbon stereogenic centers by the Mannich reaction through chiral halonium salt catalysis is presented, which provided the

• ; chiral halonium salt; contiguous stereocenters; halogen bonding; Mannich reaction; Introduction Halogen bonding (XB) has attracted intense research attention for its unique interaction between halogen atoms and electron-rich substituents [1]. XB has been applied to various fields of chemistry, such as

• diastereoselectivities with up to 97% ee (Figure 2b) [42]. To the best of our knowledge, the present paper is the first to report the asymmetric construction of β-amino cyanoesters with contiguous tetrasubstituted carbon stereogenic centers by the Mannich reaction, using our originally developed chiral halonium salt