Organocatalytic Approach for Assembling Flavanones via a Cascade 1,4-Conjugate Addition/oxa-Michael Addition between Propargylamines with Water

Xinwei He*, Mengqing Xie, Ruxue Li, Pui Ying Choy, Qiang Tang, Yongjia Shang and Fuk Yee Kwong*

*Anhui Normal University, Wuhu 241002; The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, P. R. China, Email: xinweihemail.ahnu.edu.cn, fykwongcuhk.edu.hk

X. He, M. Xie, R. Li, P. Y. Choy, Q. Tang, Y. Shang, F. Y. Kwong, Org. Lett., 2020, 22, 4306-4310.

DOI: 10.1021/acs.orglett.0c01357

---

see article for more reactions

Abstract

DBU catalyzes a sequence of 1,4-conjugate addition of water to alkynyl o-quinone methide (o-AQM), followed by an alkyne-allene isomerization and subsequent intramolecular oxa-Michael addition to provide a broad range of flavanones in very good yields with good functional-group tolerance.

see article for more examples

proposed mechanism

---

---

Key Words

Chromanones, Organocatalysis

---

ID: J54-Y2020