Details

Autor(en) / Beteiligte

• Zhang, Lin-Lin
• Zhang, Ji-Wei
• Xiang, Shao-Hua
• Guo, Zhen
• Tan, Bin

Titel

Remote Control of Axial Chirality: Synthesis of Spirooxindole–Urazoles via Desymmetrization of ATAD

Ist Teil von

• Organic letters, 2018-10, Vol.20 (19), p.6022-6026

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2018

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• For the first time, a desymmetrization strategy empowered the assembly of a class of optically pure spirooxindole–urazoles possessing an N-Ar stereogenic axis via remote control of axial chirality in an asymmetric three-component reaction. This transformation was realized by a tandem bisthiourea-catalyzed asymmetric Diels–Alder reaction and substrate-controlled asymmetric ene reaction. The driving force derived from aromatization and the high reactivity of 4-aryl-1,2,4-triazole-3,5-dione enophiles mediated the occurrence of the successive ene reaction under mild conditions.