Acid-catalyzed skeletal rearrangement of epoxy alkynes: a fast access to highly functionalized allenes.
The acid-catalyzed reaction of epoxy alkyne involves an epoxide ring-opening attacked by pi-alkyne, leading to a semipinacol-type rearrangement. In this process, a type of carbon-carbon 3,3-migration of the alkyne system has been discovered, which is promoted both by epoxide inducing and hydroxide promoting. This transformation enables the fast synthesis of allenes in mild conditions.
Zheng
Zhao-Jing
ZJ
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China.
Shu
Xing-Zhong
XZ
Ji
Ke-Gong
KG
Zhao
Shu-Chun
SC
Liang
Yong-Min
YM