Journal
ORGANIC LETTERS
Volume 18, Issue 19, Pages 5022-5025Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b02480
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Funding
- National Natural Science Foundation of China [81330075]
- China Postdoctoral Science Foundation [2015M570631, 2016T90672]
- Zhengzhou University [1511331002]
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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.
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