Application of chiral triazole-substituted iodoarenes in the enantioselective construction of spirooxazolines

Abstract

A catalytic highly enantioselective synthesis of spirooxazolines is presented. Starting from readily available 2-naphthol-substituted benzamides and using catalytic amounts of a chiral triazole-substituted iodoarene catalyst, a variety of spirooxazolines can...

Chiral Iodotriptycenes: Synthesis and Catalytic Applications

“…However, (+)‐ 16 produced the compound 20 in 28 % yield (1 % ee ) and (−)‐ 16 in 31 % yield (5 % ee ), indicating that these compounds are also not selective catalysts. The absolute configuration of the products 18 , [17n,24] 20 , [25] 22 [26] and 24 [27] were assigned using data reported in literature.…”

Chiral Iodotriptycenes: Synthesis and Catalytic Applications

“…However, (+)-16 produced the compound 20 in 28 % yield (1 % ee) and (À )-16 in 31 % yield (5 % ee), indicating that these compounds are also not selective catalysts. The absolute configuration of the products 18, [17n,24] 20, [25] 22 [26] and 24 [27] were assigned using data reported in literature.…”

Dearomatization of α-Unsubstituted β-Naphthols

“…Nevertheless, most of these reactions still rely on either intramolecular manner or intermolecular transformations of functionalized starting materials. [2][3][4][5][6][7] These processes use -substituted -naphthols (R ≠ H) bearing substituents at the  position to prevent unwanted side reactions. The oxidation coupling, -position functionalization, or [3+2]-cycloaddition reactions of -unsubstituted -naphthols are favorable pathways as their aromatic properties still been maintained.…”