Gold catalyzed diastereoselective cascade allylation/enyne cycloisomerization to construct densely functionalized oxygen heterocycles.
A new tandem allylation/enyne cycloisomerization reaction was developed to construct densely functionalized oxygen heterocycles with high diastereoselectivities from the intermolecular reaction of allylic acetates with propargylic alcohols via gold catalysis. Terminal and nonterminal propargylic alcohols take different reaction routes either to provide 3-oxa-bicyclo[4.1.0]hept-4-ene derivatives 5 or to give endocyclic rearrangement products 7 and alkoxycyclization adducts 8. Cyclopropane's stereochemistry was mainly determined by allylic substituents.
Chen
Zili
Z
Department of Chemistry, Renmin University of China, Beijing 100872, China. zilichen@ruc.edu.cn
Zhang
Yu-Xin
YX
Wang
Ya-Hui
YH
Zhu
Li-Li
LL
Liu
Heng
H
Li
Xiao-Xiao
XX
Guo
Lin
L