title: AlCl3-Catalyzed Annulations of Ynamides Involving a Torquoselective Process for the Simultaneous Control of Central and Axial Chirality.
abstract: 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 4π-electrocyclic ring opening and 6π-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.
authors.affiliation: Collaborative Innovation Center of New Drug Research and Safety Evaluation, Henan Province, School of Pharmaceutical Sciences, and College of Chemistry and Molecular Engineering, and ‡Department of Pathophysiology, School of Basic Medical Sciences, Zhengzhou University , Zhengzhou 450001, China.
authors.forename: Yanyan
authors.initials: Y
authors.lastname: Yang
authors.affiliation: Collaborative Innovation Center of New Drug Research and Safety Evaluation, Henan Province, School of Pharmaceutical Sciences, and College of Chemistry and Molecular Engineering, and ‡Department of Pathophysiology, School of Basic Medical Sciences, Zhengzhou University , Zhengzhou 450001, China.
authors.forename: Hongxu
authors.initials: H
authors.lastname: Liu
authors.affiliation: Collaborative Innovation Center of New Drug Research and Safety Evaluation, Henan Province, School of Pharmaceutical Sciences, and College of Chemistry and Molecular Engineering, and ‡Department of Pathophysiology, School of Basic Medical Sciences, Zhengzhou University , Zhengzhou 450001, China.
authors.forename: Cheng
authors.initials: C
authors.lastname: Peng
authors.affiliation: Collaborative Innovation Center of New Drug Research and Safety Evaluation, Henan Province, School of Pharmaceutical Sciences, and College of Chemistry and Molecular Engineering, and ‡Department of Pathophysiology, School of Basic Medical Sciences, Zhengzhou University , Zhengzhou 450001, China.
authors.forename: Jie
authors.initials: J
authors.lastname: Wu
authors.affiliation: Collaborative Innovation Center of New Drug Research and Safety Evaluation, Henan Province, School of Pharmaceutical Sciences, and College of Chemistry and Molecular Engineering, and ‡Department of Pathophysiology, School of Basic Medical Sciences, Zhengzhou University , Zhengzhou 450001, China.
authors.forename: Jingyi
authors.initials: J
authors.lastname: Zhang
authors.affiliation: Collaborative Innovation Center of New Drug Research and Safety Evaluation, Henan Province, School of Pharmaceutical Sciences, and College of Chemistry and Molecular Engineering, and ‡Department of Pathophysiology, School of Basic Medical Sciences, Zhengzhou University , Zhengzhou 450001, China.
authors.forename: Yan
authors.initials: Y
authors.lastname: Qiao
authors.affiliation: Collaborative Innovation Center of New Drug Research and Safety Evaluation, Henan Province, School of Pharmaceutical Sciences, and College of Chemistry and Molecular Engineering, and ‡Department of Pathophysiology, School of Basic Medical Sciences, Zhengzhou University , Zhengzhou 450001, China.
authors.forename: Xiao-Na
authors.initials: XN
authors.lastname: Wang
authors.affiliation: Collaborative Innovation Center of New Drug Research and Safety Evaluation, Henan Province, School of Pharmaceutical Sciences, and College of Chemistry and Molecular Engineering, and ‡Department of Pathophysiology, School of Basic Medical Sciences, Zhengzhou University , Zhengzhou 450001, China.
authors.forename: Junbiao
authors.initials: J
authors.lastname: Chang