AlCl3-Catalyzed Annulations of Ynamides Involving a Torquoselective Process for the Simultaneous Control of Central and Axial Chirality

作者：Yang, Yanyan; Liu, Hongxu; Peng, Cheng; Wu, Jie; Zhang, Jingyi; Qiao, Yan; Wang, Xiao-Na^*; Chang, Junbiao^*

来源：Organic Letters, 2016, 18(19): 5022-5025.

DOI：10.1021/acs.orglett.6b02480

• MAIN-GROUP THERMOCHEMISTRY
• PRIVILEGED STRUCTURES
• 2+2+2 CYCLOADDITION
• NONCOVALENT INTERACTIONS
• DENSITY FUNCTIONALS
• DRUG DISCOVERY
• DERIVATIVES
• ATROPISOMERS
• AMINATION
• NITRILES

A highly torquoselective process for simultaneous control of central and axial chirality by the annulation of terminally substituted ynamides with o-quinone methides is reported. In the presence of AlCl3, a sequence comprising a [2 + 2] cycloaddition followed by the torquoselective 4 pi-electrocyclic ring opening and 6 pi-electrocyclic ring closure leads to highly stereoselective formation of diastereoisomeric 4-amino-2H-chromenes. Terminally unsubstituted ynamides undergo AlCl3-catalyzed [4 + 2] cycloaddition with o-quinone methides providing 2-amino-4H-chromenes.

• 出版日期2016-10-7
• 单位郑州大学